JP2013112621A - Liquid crystal compound, method for producing the same, liquid crystal composition, and liquid crystal electrooptical element - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a liquid crystal compound high in compatibility with other liquid crystal materials or non-liquid crystal materials, also chemically stable, and having the property of being activated at low voltage with excellent high-speed responsiveness over a wide range of temperatures when used in a liquid crystal electrooptical element, to provide a method for producing the compound, to provide a liquid crystal composition containing the compound, and to provide a liquid crystal electrooptical element.SOLUTION: There is provided the liquid crystal compound having a -CFCHFCFO- linkage group specified by formula (1): R-(A)-Z-(A)-Z-(A)-Z-A-CFCHFCFO-A-Z-(A)-Z-(A)-R.

Description

  The present invention relates to a liquid crystal compound, a method for producing the same, a liquid crystal composition containing the compound, and a liquid crystal electro-optical element.

Liquid crystal electro-optic elements include portable devices such as mobile phones and PDAs, display devices for office automation equipment such as copying machines and personal computer monitors, display devices for home appliances such as liquid crystal televisions, clocks, calculators, measuring instruments, and automobiles. It is used for applications such as instruments and cameras, and various performances such as a wide operating temperature range, a low operating voltage, high-speed response, and chemical stability are required.
A material exhibiting a liquid crystal phase is used for such a liquid crystal electro-optical element, but at present, not all of these characteristics are satisfied with a single compound, and one or more characteristics are excellent. A plurality of liquid crystal compounds and non-liquid crystal compounds are mixed to satisfy the required performance as a liquid crystal composition.
Among various properties required for compounds used in liquid crystal compositions in the field of liquid crystal electro-optical elements, it has excellent compatibility with other liquid crystal materials or non-liquid crystal materials, is chemically stable, and It is an important issue to provide a compound or a liquid crystal composition having excellent properties of high-speed response in a wide temperature range and capable of being driven at a low voltage when used in a liquid crystal electro-optical element.

As a solution to such a problem, a —CF ₂ O— linking group-containing compound and a —CH ₂ CH ₂ CF ₂ O— linking group-containing compound have been used so far. (Patent Document 1, Patent Document 2) However, the -CF ₂ O-linking group-containing compounds, there is a problem that sometimes become -CF ₂ O-are degraded depending on the structure. Further, the —CH ₂ CH ₂ CF ₂ O— linking group-containing compound has a problem that it involves many production steps and is complicated.

Japanese Patent Laid-Open No. 05-112778 JP 2003-2858 A

The present invention has excellent compatibility with other liquid crystal materials or non-liquid crystal materials, is chemically stable, has excellent high-speed response in a wide temperature range and can be driven at a low voltage when used in a liquid crystal electro-optic element. An object is to provide a liquid crystal compound having properties and a method for producing the same. Another object of the present invention is to provide a liquid crystal compound having a large dielectric anisotropy and the like in addition to the above characteristics by adjusting each group in the liquid crystal compound.
In addition, the present invention provides a liquid crystal composition suitable for obtaining a liquid crystal electro-optical element containing the liquid crystal compound and capable of being driven at a low voltage in a wide temperature range and having a high display quality, and a liquid crystal electrolysis using the liquid crystal composition. An object is to provide an optical element.

As a result of intensive studies, the present inventors have solved the problem by providing a liquid crystal composition containing a compound having a specific structure having a —CF ₂ CHFCF ₂ O— linking group. We have found that liquid crystal electro-optic elements using materials are useful compounds that satisfy various performance requirements such as a wide operating temperature range, low operating voltage, high-speed response, and chemical stability. It was. That is, this invention provides the liquid crystal compound represented by Formula (1).
_{^{R 1 - (A 1) a}} -Z 1 - (A 2) b -Z 2 - (A 3) c -Z 3 -A 4 -CF 2 CHFCF 2 O-A 5 -Z 4 - (A 6) d _{^{-Z 5 - (A 7) e}} -R 2 (1)
The symbol in Formula (1) shows the following meanings.
R ¹ and R ^{2 are} each independently a hydrogen atom, a halogen atom, —CN, —NCS, —SF ₅ or a monovalent aliphatic hydrocarbon group having 1 to 18 carbon atoms, and one of the groups The above —CH ₂ — may be substituted with an etheric oxygen atom (—O—) or a thioetheric sulfur atom (—S—), and any hydrogen atom in the group is substituted with a fluorine atom. Also good.
A ¹ , A ² , A ³ , A ⁴ , A ⁵ , A ⁶ , A ⁷ : independently of each other, trans-1,4-cyclohexylene group, 1,4-cyclohexenylene group, 1, 3 -Cyclobutylene group, 1,2-cyclopropylene group, naphthalene-2,6-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, decahydronaphthalene-2,6-diyl group Or 1,4-phenylene group. One or more hydrogen atoms in the group may be substituted with a halogen atom, and one or two ═CH— groups present in the group may be substituted with a nitrogen atom. Two —CH ₂ — groups may be substituted with —O— or —S—.
Z ¹ , Z ² , Z ³ , Z ⁴ , Z ⁵ : each independently a single bond, a divalent aliphatic hydrocarbon group having 1 to 4 carbon atoms, and one or more —CH in the group ₂ — may be substituted with —O— or —S—, and any hydrogen in the group may be substituted with fluorine.
a, b, c, d, e: 0 or 1 independently of each other. However, 0 ≦ a + b + c + d + e ≦ 3.

Among the liquid crystal compounds represented by the formula (1), compounds represented by the following formula (1-1) are preferable.
_{^{R 11 - (A 11) a}} -Z 11 - (A 21) b -Z 21 - (A 31) c -Z 31 -A 41 -CF 2 CHFCF 2 O-A 51 -Z 41 - (A 61) d _{^{-Z 51 - (A 71) e}} -R 21 (1-1)
The symbols in the formula have the following meanings.
R ¹¹ and R ^{21 are} each independently a hydrogen atom, a fluorine atom, —SF ₅ , an alkyl group having 1 to 18 carbon atoms, or an alkenyl group having 2 to 18 carbon atoms. One or more —CH ₂ — in the group may be substituted with —O— or —S—, and one or more hydrogen atoms in the group may be substituted with a fluorine atom.
A ¹¹ , A ²¹ , A ³¹ , A ⁴¹ , A ⁵¹ , A ⁶¹ , A ⁷¹ : Independently of each other, a trans-1,4-cyclohexylene group or a 1,4-phenylene group. One or more hydrogen atoms in the group may be substituted with a halogen atom, and one or two ═CH— groups present in the group may be substituted with a nitrogen atom. One —CH ₂ — group may be substituted with —O— or —S—.
Z ¹¹ , Z ²¹ , Z ³¹ , Z ⁴¹ , Z ^{51 are} each independently a single bond or an alkylene group having 1 to 4 carbon atoms, and one or more —CH ₂ — in the group is —O—. And one or more hydrogen atoms in the group may be substituted with a fluorine atom.
a, b, c, d and e have the same meaning as described above.

Among the liquid crystal compounds represented by the formula (1), a compound represented by the following formula (1-2) is preferable.
_{^{R 12 - (A 12) a}} -Z 12 - (A 22) b -Z 22 - (A 32) c -Z 32 -A 42 -CF 2 CHFCF 2 O-A 52 -Z 42 - (A 62) d _{^{-Z 52 - (A 72) e}} -R 22 (1-2)
The symbols in the formula have the following meanings.
R ¹² : a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or a substituted alkyl group having 1 to 10 carbon atoms.
R ²² : a fluorine atom, —SF ₅ , a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or a substituted alkyl group having 1 to 10 carbon atoms.
A ¹² , A ²² , A ³² , A ⁵² , A ⁶² , A ⁷² : independently of each other, a trans-1,4-cyclohexylene group or a 1,4-phenylene group. One or more hydrogen atoms in the group may be substituted with a halogen atom, and one or two ═CH— groups present in the group may be substituted with a nitrogen atom. One —CH ₂ — group may be substituted with —O— or —S—.
^A42 : trans-1,4-cyclohexylene group. One or more hydrogen atoms in the group may be substituted with a halogen atom, and one or two —CH ₂ — groups may be substituted with —O— or —S—.
Z ¹² , Z ²² , Z ³² , Z ⁴² , Z ⁵² : each independently a single bond or an alkylene group having 1 to 4 carbon atoms.
a, b, c, d and e have the same meaning as described above.

The method for producing the liquid crystal compound represented by the formula (1) is represented by the formula (1) by reacting a compound represented by the following formula (2) with a compound represented by the following formula (3). Preferred is a method for obtaining a compound.
_{^{R 1 - (A 1) a}} -Z 1 - (A 2) b -Z 2 - (A 3) c -Z 3 -A 4 -X (2)
CF ₂ = CFCF ₂ O—A ⁵ —Z ⁴ — (A ⁶ ) _d —Z ⁵ — (A ⁷ ) _e —R ² (3)
R ¹ , R ² , A ¹ , A ² , A ³ , A ⁴ , A ⁵ , A ⁶ , A ⁷ , Z ¹ , Z ² , Z ³ , Z ⁴ , in Formula (2) and Formula (3) Z ⁵ , a, b, c, d and e have the same meaning as described above. X is a halogen atom.

Among these, when A ⁴ is a trans-1,4-cyclohexylene group, a method including the following step 1 and step 2 is preferable. In Step 2, it is preferable not to include a copper reagent.
Step 1: A step of reacting a compound represented by the following formula (2 ′) with metallic magnesium to obtain a compound represented by the following formula (4).
Step 2: A step of synthesizing a compound represented by the following formula (1 ′) by reacting a compound represented by the following formula (4) with a compound represented by the following formula (3).
_{^{R 1 - (A 1) a}} -Z 1 - (A 2) b -Z 2 - (A 3) c -Z 3 -Cy-X (2 ')
_{^{R 1 - (A 1) a}} -Z 1 - (A 2) b -Z 2 - (A 3) c -Z 3 -Cy-MgX (4)
CF ₂ = CFCF ₂ O—A ⁵ —Z ⁴ — (A ⁶ ) _d —Z ⁵ — (A ⁷ ) _e —R ² (3)
_{^{R 1 - (A 1) a}} -Z 1 - (A 2) b -Z 2 - (A 3) c -Z 3 -Cy-CF 2 CHFCF 2 O-A 5 -Z 4 - (A 6) d - Z ^5- (A ⁷ ) _e -R ² (1 ')
In the formula, -Cy- is a trans-1,4-cyclohexylene group, and other symbols have the same meaning as described above.

  The present invention also provides a liquid crystal composition comprising the liquid crystal compound (1) represented by the formula (1).

  The present invention also provides a liquid crystal electro-optical element formed by sealing the liquid crystal composition between two substrates provided with electrodes.

The liquid crystal compound represented by the formula (1) of the present invention is excellent in compatibility with other liquid crystal materials or non-liquid crystal materials, and is chemically stable. In addition, the compound of the present invention has various performances required for the liquid crystal electro-optic element, specifically, for example, a wide operating temperature by appropriately selecting the ring group, substituent and linking group constituting the compound. A liquid crystal composition satisfying the range, low operating voltage, high-speed response, chemical stability, and the like can be prepared. In addition, when the liquid crystal composition is used in a liquid crystal electro-optical element, it can be driven at a low voltage with excellent high-speed response in a wide temperature range.
According to the production method of the present invention, a compound having a —CF ₂ CHFCF ₂ O— linking group is highly versatile and can be easily and efficiently produced easily and efficiently industrially.

The present invention will be described in more detail below.
In this specification, the liquid crystal compound represented by the formula (1) is referred to as a compound (1), and the compounds represented by other formulas are also described in the same manner.

In the compound (1) of the present invention, R ¹ and R ² are each independently a hydrogen atom, a halogen atom, —CN, —NCS, —SF ₅ or a monovalent aliphatic carbon atom having 1 to 18 carbon atoms. A hydrogen group, and one or more —CH ₂ — in the group may be substituted with —O— or —S—, and any hydrogen atom in the group may be substituted with a fluorine atom. In addition, both of these groups and hydrogen atom substitution may be included.
Hereinafter, an alkyl group including substitution with at least one of —O—, —S— and a fluorine atom is referred to as a “substituted alkyl group”.
An alkenyl group containing a substitution with at least one of —O—, —S— and a fluorine atom is referred to as a “substituted alkenyl group”.

Examples of the monovalent aliphatic hydrocarbon group include an alkyl group, an alkenyl group, and an alkynyl group, and among them, an alkyl group or an alkenyl group is preferable.
Examples of the substituted alkyl group include an alkoxy group, an alkoxyalkyl group, an alkylthio group, an alkylthioalkyl group, a fluoroalkyl group, a fluoroalkoxy group, a fluoroalkoxyalkyl group, and a fluoroalkylthio group.
Examples of the substituted alkenyl group include an alkenyloxy group, an alkenyloxyalkyl group, an alkenylthio group, an alkenylthioalkyl group, a fluoroalkenyl group, and a fluoroalkenyloxy group.

Examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, and a decyl group.
Examples of the alkoxy group include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentoxy group, a heptyloxy group, and an octyloxy group.
Examples of the alkoxyalkyl group include a methoxymethyl group, an ethoxymethyl group, a propoxymethyl group, a propoxyethyl group, a methoxypropyl group, an ethoxypropyl group, and a propoxypropyl group.
Examples of the alkylthio group include a methylthio group, an ethylthio group, a propylthio group, a butylthio group, a pentylthio group, a hexylthio group, a heptylthio group, and an octylthio group.
Alkylthioalkyl groups include methylthiomethyl, ethylthiomethyl, propylthiomethyl, butylthiomethyl, methylthioethyl, ethylthioethyl, propylthioethyl, methylthiopropyl, ethylthiopropyl, propylthio A propyl group etc. are mentioned.
Examples of the alkenyl group include a vinyl group, 1-propenyl group, 1-butenyl group, 1-pentenyl group, 3-butenyl group, and 3-pentenyl group.
Examples of the alkenyloxy group include an allyloxy group.
Fluoroalkyl groups include trifluoromethyl, fluoromethyl, 2-fluoroethyl, difluoromethyl, 2,2,2-trifluoroethyl, 1,1,2,2-tetrafluoroethyl, 2 -Fluoroethyl group, 3-fluoropropyl group, 4-fluorobutyl group, 5-fluoropentyl group and the like can be mentioned.
Fluoroalkoxy groups include fluoromethoxy group, trifluoromethoxy group, difluoromethoxy group, pentafluoroethoxy group, 1,1,2,2-tetrafluoroethoxy group, heptafluoropropoxy group, 1,1,2,3, Examples include 3,3-hexafluoropropoxy group.
Examples of the fluoroalkoxyalkyl group include a trifluoromethoxymethyl group.
As the fluoroalkenyl group, 2-fluoroethenyl group, 2,2-difluoroethenyl group, 1,2,2-trifluoroethenyl group, 3-fluoro-1-butenyl group, 4-fluoro-1-butenyl group Etc.
Examples of the fluoroalkylthio group include a trifluoromethylthio group, a difluoromethylthio group, a 1,1,2,2-tetrafluoroethylthio group, a 2,2,2-trifluoroethylthio group, and the like.

R ¹ and R ² are hydrogen atom, halogen atom, —CN, —NCS, —SF ₅ , alkyl group, alkenyl group, alkoxy group, alkoxyalkyl group, alkylthio group, alkylthioalkyl group, alkenyl group, alkenyloxy group. , An alkenylthio group, a fluoroalkyl group, a fluoroalkoxy group, a fluoroalkoxyalkyl group, a fluoroalkyl group, and a fluoroalkenylthio group are preferred.

Among these, as R ¹ and R ² , since reactivity and side reaction are unlikely to occur, a hydrogen atom, a fluorine atom, —SF ₅ , an alkyl group having 1 to 18 carbon atoms, an alkenyl group having 2 to 18 carbon atoms, A substituted alkyl group having 1 to 18 carbon atoms and a substituted alkenyl group having 2 to 18 carbon atoms are preferable.

In particular, R ¹ is particularly preferably a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or a substituted alkyl group having 1 to 10 carbon atoms.
R ² is particularly preferably a fluorine atom, —SF ₅ , a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or a substituted alkyl group having 1 to 10 carbon atoms.

In the compound (1), A ¹ , A ² , A ³ , A ⁴ , A ⁵ , A ⁶ and A ⁷ are independently of each other a trans-1,4-cyclohexylene group, 1,4-cyclohexene. Senylene group, 1,3-cyclobutylene group, 1,2-cyclopropylene group, naphthalene-2,6-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, decahydronaphthalene It is a -2,6-diyl group or a 1,4-phenylene group.
One or more hydrogen atoms in each of these groups A ^{1 to} A ⁷ may be substituted with a halogen atom, and one or two of the ═CH— groups constituting each ring of A ^{1 to} A ⁷ are It may be substituted with a nitrogen atom, and one or two —CH ₂ — groups may be substituted with —O—, —S—, and may contain any of these groups and hydrogen atoms. Good. For a group containing such a substitution, the term “substituted” is added to the front of each ring group name, for example, “substituted 1,4-phenylene group”, “substituted trans-1,4-cyclohexylene group”, etc. May be called. The halogen atom here is preferably a chlorine atom or a fluorine atom.

When A ^{1 to} A ⁷ are 1,4-phenylene groups and further have a halogen atom as a substituent, the number of halogen atoms substituted by one 1,4-phenylene group is 1 to 4 Among these, one or two is preferable. When it is a trans-1,4-cyclohexylene group and further has a halogen atom as a substituent, the number of halogen atoms to be substituted is preferably 1 to 4. The halogen atom may be bonded to the 1st or 4th carbon atom of the cyclohexylene group.
Examples of the 1,4-phenylene group substituted with a nitrogen atom include 2,5-pyrimidinylene group and 2,5-pyridinylene group.
Examples of the substituted trans-1,4-cyclohexylene group by —O— or —S— include 1,3-dioxane-2,5-diyl group and 1,3-dithian-2,5-diyl group. It is done.

As A ¹ , A ² , A ³ , A ⁴ , A ⁵ , A ⁶ and A ⁷ , trans-1,4-cyclohexylene group, 1,4-phenylene group, A substituted trans-1,4-cyclohexylene group and a substituted 1,4-phenylene group are preferred.
Among them, A ¹ , A ² , A ³ , A ⁵ , A ⁶ and A ⁷ are substituted with a trans-1,4-cyclohexylene group, 1,4-phenylene group, and one or two fluorine atoms. The 1,4-phenylene group is particularly preferred.
As A ⁴ , a trans-1,4-cyclohexylene group and a substituted trans-1,4-cyclohexylene group are preferable, and a trans-1,4-cyclohexylene group is particularly preferable.

In the compound (1), Z ¹ , Z ² , Z ³ , Z ⁴ and Z ⁵ are each independently a single bond, a divalent aliphatic hydrocarbon group having 1 to 4 carbon atoms, One or more —CH ₂ — in the group may be substituted with —O— or —S—, and one or more hydrogen atoms in the group may be substituted with a fluorine atom. Any substitution of hydrogen atoms may be included. A group having such substitution may be referred to with the word “substitution”. Examples of the divalent aliphatic hydrocarbon group include an alkylene group, an alkenylene group, and an alkynylene group, and among them, an alkylene group is preferable.
The substituted alkylene _{group, -CF 2 CF 2 -, -} CF 2 CH 2 -, - CH 2 CF 2 -, - CHFCH 2 -, - CH 2 CHF -, - CF 2 CHF -, - CHFCF 2 -, - CH ₂ O—, —OCH ₂ —, —CH ₂ S—, —SCH ₂ —, —CF ₂ O—, —OCF ₂ —, —CF ₂ CF ₂ CF ₂ CF ₂ —, —OCF ₂ CF ₂ O— _{, -C 2 H 4 CF 2 O-} , and the like.
Further, when Z ¹ , Z ² , Z ³ , Z ⁴ or Z ⁵ is a single bond, it means that groups existing on both sides of each group are directly bonded. For example, when Z ¹ is a single bond and a and b are 1, A ¹ and A ² are directly bonded. When Z ¹ , Z ² and Z ³ are single bonds and a, b and c are 0, R ¹ and A ⁴ are directly bonded.

Z ¹ , Z ² , Z ³ , Z ⁴ and Z ⁵ are each a single bond, an alkylene group having 1 to 4 carbon atoms, a fluorine-substituted alkylene group corresponding to the group, or —O— for ease of synthesis or the like. A substituted alkylene group is preferred.
Among these, a single bond and an alkylene group having 1 to 4 carbon atoms are particularly preferable.

In the compound (1) of the present invention, a, b, c, d and e are 0 or 1 independently of each other.
However, 0 ≦ a + b + c + d + e ≦ 3.
a, b, c, d and e can be appropriately selected according to the properties required of the compound.
For example, when importance is attached to the fact that the compound (1) has low viscosity or the compound is excellent in compatibility with other liquid crystal materials or non-liquid crystal materials, 0 ≦ a + b + c + d + e ≦ 1 is preferable. On the other hand, when emphasizing the high liquid crystal temperature range of the compound, it is preferable that 1 ≦ a + b + c + d + e ≦ 3.

Compound (1) From the viewpoint of increasing the maximum temperature of the liquid crystal phase and decreasing the viscosity, A ¹ , A ² , A ³ , A ⁴ , A ⁵ , A ⁶ and A ⁷ are trans-1,4-cyclohexylene groups. 1,4-phenylene group is preferable. R ¹ and R ² are preferably an alkyl group, an alkenyl group, or an alkoxy group.

From the viewpoint of positively increasing Δε of the compound (1), “—A ⁵ —Z ⁴ — (A ⁶ ) _d —Z ⁵ — (A ⁷ ), which is the O-side linking group of —CF ₂ CHFCF ₂ O—. ) _E -R < ² >"is preferably an electron withdrawing group. The electron withdrawing property of “−A ⁵ —Z ⁴ — (A ⁶ ) _d —Z ⁵ — (A ⁷ ) _e —R ² ” means that in compound (1), d = e = 0, Z ⁴ and It is more electron withdrawing than “—A ⁵ —R ² ” in which Z ⁵ is a single bond and R ² is a hydrogen atom and A ⁵ is an unsubstituted phenylene group or cyclohexylene group. means.

In the case where “—A ⁵ —Z ⁴ — (A ⁶ ) _d —Z ⁵ — (A ⁷ ) _e —R ² ” is an electron withdrawing group, it is mentioned that each group is as follows. It is done.

R ² : fluorine atom, —OCF ₃ , —OCF ₂ H, —CN, —NCS, or —SF ₅
A ⁵ , A ⁶ , A ⁷ : independently of each other, a 1,4-phenylene group, a 2-fluoro-1,4-phenylene group, or a 2,6-difluoro-1,4-phenylene group.
Z ⁴ , Z ⁵ : single bond d, e: 0 or 1 independently of each other
The substitution positions of the substituted ring groups in A ⁵ , A ⁶ and A ⁷ are the 4th position closer to R ¹ and the 1st position closer to R ² .

From the viewpoint of negatively increasing Δε of the compound (1), one or more of A ¹ , A ² , A ³ , A ⁴ , A ⁵ , A ⁶ and A ⁷ are 2,3-difluoro-1,4- A phenylene group is preferred. R ¹ and R ² directly bonded to the 2,3-difluoro-1,4-phenylene group are preferably alkoxy groups.

As the compound (1) of the present invention, the compound (1-1) is preferable.
_{^{R 11 - (A 11) a}} -Z 11 - (A 21) b -Z 21 - (A 31) c -Z 31 -A 41 -CF 2 CHFCF 2 O-A 51 -Z 41 - (A 61) d _{^{-Z 51 - (A 71) e}} -R 21 (1-1)
The symbols in the formula have the following meanings.
R ¹¹ and R ^{21 are} each independently a hydrogen atom, a fluorine atom, —SF ₅ , an alkyl group having 1 to 18 carbon atoms, or an alkenyl group having 2 to 18 carbon atoms. One or more —CH ₂ — in the group may be substituted with —O— or —S—, and one or more hydrogen atoms in the group may be substituted with a fluorine atom.
A ¹¹ , A ²¹ , A ³¹ , A ⁴¹ , A ⁵¹ , A ⁶¹ , A ⁷¹ : Independently of each other, a trans-1,4-cyclohexylene group or a 1,4-phenylene group. One or more hydrogen atoms in the group may be substituted with a halogen atom, and one or two ═CH— groups present in the group may be substituted with a nitrogen atom. One —CH ₂ — group may be substituted with —O— or —S—.
Z ¹¹ , Z ²¹ , Z ³¹ , Z ⁴¹ , Z ^{51 are} each independently a single bond or an alkylene group having 1 to 4 carbon atoms, and one or more —CH ₂ — in the group is —O—. And one or more hydrogen atoms in the group may be substituted with a fluorine atom.
a, b, c, d and e have the same meaning as described above.

As the compound (1) of the present invention, the compound (1-2) is more preferable.
_{^{R 12 - (A 12) a}} -Z 12 - (A 22) b -Z 22 - (A 32) c -Z 32 -A 42 -CF 2 CHFCF 2 O-A 52 -Z 42 - (A 62) d _{^{-Z 52 - (A 72) e}} -R 22 (1-2)
The symbols in the formula have the following meanings.
R ¹² : a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or a substituted alkyl group having 1 to 10 carbon atoms.
R ²² : a fluorine atom, —SF ₅ , a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or a substituted alkyl group having 1 to 10 carbon atoms.
A ¹² , A ²² , A ³² , A ⁵² , A ⁶² , A ⁷² : independently of each other, a trans-1,4-cyclohexylene group or a 1,4-phenylene group. One or more hydrogen atoms in the group may be substituted with a halogen atom, and one or two ═CH— groups present in the group may be substituted with a nitrogen atom. One —CH ₂ — group may be substituted with —O— or —S—.
^A42 : trans-1,4-cyclohexylene group. One or more hydrogen atoms in the group may be substituted with a halogen atom, and one or two —CH ₂ — groups may be substituted with —O— or —S—.
Z ¹² , Z ²² , Z ³² , Z ⁴² , Z ⁵² : each independently a single bond or an alkylene group having 1 to 4 carbon atoms.
a, b, c, d and e have the same meaning as described above.

The method for producing the compound (1) of the present invention is preferably a method for obtaining the compound (1) by reacting the compound (2) with the compound (3).
_{^{R 1 - (A 1) a}} -Z 1 - (A 2) b -Z 2 - (A 3) c -Z 3 -A 4 -X (2)
CF ₂ = CFCF ₂ O—A ⁵ —Z ⁴ — (A ⁶ ) _d —Z ⁵ — (A ⁷ ) _e —R ² (3)
R ¹ , R ² , A ¹ , A ² , A ³ , A ⁴ , A ⁵ , A ⁶ , A ⁷ , Z ¹ , Z ² , Z ³ , Z ⁴ , in Formula (2) and Formula (3) Z ⁵ , a, b, c, d and e have the same meaning as described above. X is a halogen atom.

Among these, when A ⁴ is a trans-1,4-cyclohexylene group, a method including the following step 1 and step 2 is preferable. In Step 2, it is preferable not to include a copper reagent.
Step 1: A step of reacting compound (2 ′) with metallic magnesium to give compound (4).
Step 2: A step of synthesizing compound (1 ′) by reacting compound (4) with compound (3).
_{^{R 1 - (A 1) a}} -Z 1 - (A 2) b -Z 2 - (A 3) c -Z 3 -Cy-X (2 ')
_{^{R 1 - (A 1) a}} -Z 1 - (A 2) b -Z 2 - (A 3) c -Z 3 -Cy-MgX (4)
CF ₂ = CFCF ₂ O—A ⁵ —Z ⁴ — (A ⁶ ) _d —Z ⁵ — (A ⁷ ) _e —R ² (3)
_{^{R 1 - (A 1) a}} -Z 1 - (A 2) b -Z 2 - (A 3) c -Z 3 -Cy-CF 2 CHFCF 2 O-A 5 -Z 4 - (A 6) d - Z ^5- (A ⁷ ) _e -R ² (1 ')
In the formula, -Cy- is a trans-1,4-cyclohexylene group, and other symbols have the same meaning as described above.

  Compound (2) can be easily obtained by a method described in a book on organic synthesis, such as a commercially available product or a new experimental chemistry course (published by Maruzen Co., Ltd.).

  Compound (3) can be produced by the method described in International Publication No. 2004/058676.

  The production method of the present invention is preferably carried out in a solvent. Solvents include aromatic hydrocarbon solvents such as benzene, toluene, xylene, and ethylbenzene, aliphatic hydrocarbon solvents such as pentane, hexane, heptane, and octane; tetrahydrofuran, diethyl ether, diisopropyl ether, dibutyl ether, and t-butylmethyl. Ether solvents such as ether and dimethoxyethane; petroleum ethers or a suitable mixed solvent of the above solvents can be used. Among these, ether solvents such as tetrahydrofuran, diethyl ether and t-butyl methyl ether, and mixed solvents of ether solvents and aliphatic hydrocarbon solvents are preferable.

The production method of the present invention is preferably carried out using a metal reagent or a radical initiator. As the metal reagent, metal lithium, metal magnesium, zinc powder, copper powder, alkyl lithium reagents such as butyl lithium, alkyl magnesium halide and the like are preferable. As the radical initiator, boron compounds such as triethylborane, peroxides such as m-chloroperbenzoic acid and benzoyl peroxide, and diazo compounds such as azobisisobutyronitrile are preferable.
Among these, when A ⁴ is a trans-1,4-cyclohexylene group, it is preferable to use magnesium metal as step 1.

When a radical initiator is used, a tin compound such as Bu ₃ SnH or a silicon compound such as (Me ₃ Si) ₃ SiH or Ph ₂ SiH ₂ may be added as a hydrogen source.

  The reaction temperature is preferably −70 to 50 ° C., more preferably −10 to 70 ° C.

  The reaction time is preferably 0.1 to 48 hours, more preferably 1 to 24 hours.

In the production method of the present invention, the case where the compound (2) is the following compound (2-1) and the compound (3) is the following compound (3-1) is preferable.
_{^{R 11 - (A 11) a}} -Z 11 - (A 21) b -Z 21 - (A 31) c -Z 31 -A 41 -X (2-1)
_{CF 2 = CFCF 2 O-A} 51 -Z 41 - (A 61) d -Z 51 - (A 71) e -R 21 (3-1)
The symbols in each formula have the same meaning as described above.
When A ⁴¹ is a trans-1,4-cyclohexylene group, in step 1 and step 2, compound (2 ′) is the following compound (2′-1), and compound (4) is the following: It is a case where it is a compound (4-1), a compound (3) is the following compound (3-1), and a compound (1) is a compound (1'-1).
_{^{R 11 - (A 11) a}} -Z 11 - (A 21) b -Z 21 - (A 31) c -Z 31 -Cy-X (2'-1)
_{^{R 11 - (A 11) a}} -Z 11 - (A 21) b -Z 21 - (A 31) c -Z 31 -Cy-MgX (4-1)
_{CF 2 = CFCF 2 O-A} 51 -Z 41 - (A 61) d -Z 51 - (A 71) e -R 21 (3-1)
_{^{R 11 - (A 11) a}} -Z 11 - (A 21) b -Z 21 - (A 31) c -Z 31 -Cy-CF 2 CHFCF 2 O-A 51 -Z 41 - (A 61) d - Z ^51- (A ⁷¹ ) _e -R ²¹ (1′-1)
The symbols in each formula have the same meaning as described above.

In the production method of the present invention, it is particularly preferred that the compound (2) is the following compound (2-2) and the compound (3) is the following compound (3-2).
_{^{R 12 - (A 12) a}} -Z 12 - (A 22) b -Z 22 - (A 32) c -Z 32 -A 42 -X (2-2)
_{CF 2 = CFCF 2 O-A} 52 -Z 42 - (A 62) d -Z 52 - (A 72) e -R 22 (3-2)
The symbols in each formula have the same meaning as described above.
When A ⁴² is a trans-1,4-cyclohexylene group, in step 1 and step 2, compound (2 ′) is the following compound (2′-2) and compound (4) is the following: Preferred is the case where it is the compound (4-2), the compound (3) is the following compound (3-2), and the compound (1) is the compound (1′-2).
_{^{R 12 - (A 12) a}} -Z 12 - (A 22) b -Z 22 - (A 32) c -Z 32 -Cy-X (2'-2)
_{^{R 12 - (A 12) a}} -Z 12 - (A 22) b -Z 22 - (A 32) c -Z 32 -Cy-MgX (4-2)
_{CF 2 = CFCF 2 O-A} 52 -Z 42 - (A 62) d -Z 52 - (A 72) e -R 22 (3-2)
_{^{R 12 - (A 12) a}} -Z 12 - (A 22) b -Z 22 - (A 32) c -Z 32 -Cy-CF 2 CHFCF 2 O-A 52 -Z 42 - (A 62) d - Z ^52- (A ⁷² ) _e -R ²² (1'-2)
The symbols in each formula have the same meaning as described above.

  The present invention also provides a liquid crystal composition comprising the compound (1). This liquid crystal composition is constituted by mixing the compound (1) of the present invention with other liquid crystal compounds or non-liquid crystal compounds (collectively referred to as “other compounds”).

  The content of the compound (1) in the liquid crystal composition of the present invention can be appropriately changed depending on the purpose of use, the purpose of use, the type of other compounds, and the like. 5-50 mass% is preferable, and 2-20 mass% is especially preferable. Moreover, you may contain 2 or more types of compounds (1) in a liquid-crystal composition by a use, a use purpose, etc. In that case, 0.5-80 mass% is preferable with the total amount of a compound (1) with respect to the whole quantity of a liquid-crystal composition, and 2-50 mass% is especially preferable.

  Other compounds used in combination with the compound (1) include components for adjusting the refractive index anisotropy value, components for reducing the viscosity, components exhibiting liquid crystallinity at low temperatures, components for improving the dielectric anisotropy, and cholesteric A component for imparting properties, a component exhibiting dichroism, a component for imparting conductivity, and various other additives. These are appropriately selected depending on the application, required performance and the like, but usually those composed of a liquid crystal compound, a main component having a similar structure to the liquid crystal compound, and an additive component added if necessary.

In the liquid crystal composition of the present invention, examples of the other compound include those represented by the following formulae. In the following formulae, R ³ and R ⁴ represent a group such as an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, a halogen atom or a cyano group. R ³ and R ⁴ may be the same or different from each other.
In the following formulas, -Cy- represents a trans-1,4-cyclohexylene group, -Ph- represents a 1,4-phenylene group, and -PhFF- represents a difluorophenylene group.

R ³ -Cy-Cy-R ⁴
R ³ -Cy-Ph-R ⁴
R ³ -Cy-PhFF-CN
R ³ -Ph-Ph-R ⁴
R ³ —Ph—C≡C—Ph—R ⁴
R ³ -Cy-COO-Ph-R ^{4
R 3 -Cy-COO-PhFF-} CN
R ³ —Ph—COO—Ph—R ⁴
R ³ -Ph-COO-PhFF-CN
R ³ —Cy—CH═CH—Ph—R ⁴
R ³ —Ph—CH═CH—Ph—R ⁴
R ³ —Ph—CF═CF—Ph—R ⁴
R ³ —Cy—CF═CF—Ph—R ⁴
R ³ —Cy—CF═CF—Cy—R ⁴
R ³ —Cy—Ph—CF═CF—Ph—R ⁴
R ³ —Cy—Ph—CF═CF—Cy—R ⁴

R ³ —Ph—Cy—CF═CF—Cy—R ⁴
R ³ —Cy—Cy—CF═CF—Ph—R ⁴
R ³ —Ph—Ph—CF═CF—Ph—R ^{4
_{R 3 -Cy-CH 2 CH 2}} -Ph-R 4
_{^{R 3 -Cy-Ph-CH 2}} CH 2 -Ph-R 4
_{^{R 3 -Cy-Ph-CH 2}} CH 2 -Cy-R 4
_{^{R 3 -Cy-Cy-CH 2}} CH 2 -Ph-R 4
_{^{R 3 -Ph-CH 2 CH 2}} -Ph-R 4
_{^{R 3 -Ph-Ph-CH 2}} CH 2 -Ph-R 4
_{^{R 3 -Ph-Ph-CH 2}} CH 2 -Cy-R 4
R ³ -Cy-Ph-Ph-R ⁴
R ³ -Cy-Ph-PhFF-CN
R ³ -Cy-Ph-C≡C-Ph-R ⁴
R ³ -Cy-Ph-C≡C-PhFF-CN
R ³ -Cy-Ph-C≡C-Ph-Cy-R ⁴
R ³ —Cy—CH ₂ CH ₂ —Ph—C≡C—Ph—R ⁴

R ³ —Cy—CH ₂ CH ₂ —Ph—C≡C—Ph—Cy—R ⁴
R ³ -Cy-Ph-Ph-Cy-R ⁴
R ³ -Ph-Ph-Ph-R ⁴
R ³ —Ph—Ph—C≡C—Ph—R ⁴
R ³ —Ph—CH ₂ CH ₂ —Ph—C≡C—Ph—R ⁴
R ³ —Ph—CH ₂ CH ₂ —Ph—C≡C—Ph—Cy—R ^{4
R 3 -Cy-COO-Ph-} Ph-R 4
^{R 3 -Cy-COO-Ph-} PhFF-CN
^{R 3 -Cy-Ph-COO-} Ph-R 4
^{R 3 -Cy-Ph-COO-} PhFF-CN
^{R 3 -Cy-COO-Ph-} COO-Ph-R
^{R 3 -Cy-COO-Ph-} COO-PhFF-CN
^{R 3 -Ph-COO-Ph-} COO-Ph-R 4
^{R 3 -Ph-COO-Ph-} OCO-Ph-R 4
R ³ —Ph—CF ₂ O—Ph—R ⁴

R ³ —Cy—CF ₂ O—Ph—R ⁴
R ³ —Ph—CF ₂ O—Cy—R ^{4
_{R 3 -Cy-Ph-CF 2}} O-Ph-R 4
_{^{R 3 -Cy-Ph-CF 2}} O-Cy-R 4
_{^{R 3 -Cy-Cy-CF 2}} O-Ph-R 4
_{^{R 3 -Ph-Ph-CF 2}} O-Ph-R 4
_{^{R 3 -Ph-Ph-CF 2}} O-Cy-R 4
_{^{R 3 -Cy-Ph-CF 2}} O-PhFF-R 4
R ³ -Cy-PhFF-CF ₂ O-PhFF-R ^{4
_{R 3 -Ph-Ph-CF 2}} O-PhFF-R 4
R ³ -Ph-PhFF-CF ₂ O-PhFF-R ^{4
_{R 3 -Ph-CF 2 CF 2}} -Ph-R 4

^{_{R 3 -Cy-CF 2 CF 2}} -Ph-R 4
R ³ —Cy—CF ₂ CF ₂ —Cy—R ^{4
_{R 3 -Cy-Ph-CF 2}} CF 2 -Ph-R 4
_{^{R 3 -Cy-Ph-CF 2}} CF 2 -Cy-R 4
_{^{R 3 -Cy-Cy-CF 2}} CF 2 -Ph-R 4
_{^{R 3 -Ph-Ph-CF 2}} CF 2 -Ph-R 4
_{^{R 3 -Ph-Ph-CF 2}} CF 2 -Cy-R 4

These compounds are merely representative examples, and a hydrogen atom present in a ring structure or a terminal group in the compound may be substituted with a halogen atom, a cyano group, a methyl group, or the like. In addition, the cyclohexane ring or the benzene ring may be substituted with another 6-membered ring or 5-membered ring, for example, a pyrimidine ring or a dioxane ring. Changed to a divalent linking group such as —CH ₂ O—, —CH═CH—, —N═N—, —CH═N—, —COOCH ₂ —, —OCOCH ₂ — or —COCH ₂ —, etc. It can be selected according to the desired performance.

  Furthermore, the present invention provides a liquid crystal electro-optical element that uses the liquid crystal composition as a constituent material of a liquid crystal layer. In this specification, the liquid crystal electro-optical element is not limited to a display element, but various functional elements that use the electrical or optical characteristics of liquid crystal, for example, a liquid crystal display element, a light control window, an optical shutter, and a polarization It includes elements used for applications such as conversion elements and variable focus lenses. For example, a liquid crystal electro-optical element having an electro-optical element portion formed by sandwiching a liquid crystal layer formed by, for example, injecting the liquid crystal composition of the present invention into a liquid crystal cell between two substrates having electrodes. I will provide a. This liquid crystal electro-optic element is a twisted nematic (TN) method, a super twisted nematic (STN) method, an ECB mode, a VA mode, a guest host method, a dynamic scattering method, a phase change method, a DAP method, a dual frequency drive method, a strong Examples include those driven in various modes such as a dielectric liquid crystal display system.

A typical liquid crystal electro-optic element includes a twisted nematic (TN) type liquid crystal display element. The twisted nematic (TN) type liquid crystal display device, first, plastics, onto a substrate such as glass, of SiO _2, Al ₂ O undercoat layer or a color filter layer, such as ₃ to form optionally, an In ₂ O _A film made of _3- SnO ₂ (ITO), SnO ₂ or the like is formed, and an electrode having a required pattern is formed by photolithography or the like. Next, if necessary, an overcoat layer of polyimide, polyamide, SiO ₂ , Al ₂ O ₃ or the like is formed and oriented. A sealing material is printed on this, it arrange | positions so that an electrode surface may mutually oppose, a periphery is sealed, a sealing material is hardened, and an empty cell is formed.

  Furthermore, the composition of the present invention is injected into an empty cell, and the injection port is sealed with a sealant to form a liquid crystal cell. If necessary, this liquid crystal cell is laminated with a polarizing plate, a color polarizing plate, a light source, a color filter, a transflective plate, a reflecting plate, a light guide plate, an ultraviolet cut filter, etc., printing characters, figures, etc., non-glare processing, etc. Thus, a liquid crystal electro-optical element can be obtained.

  Note that the above description describes the basic configuration and manufacturing method of the liquid crystal electro-optical element, and other configurations can be employed. For example, a substrate using a two-layer electrode, a two-layer liquid crystal cell having a two-layer liquid crystal layer, a substrate using a reflective electrode, an active matrix device using an active matrix substrate having an active element such as a TFT or MIM, etc. Various configurations can be employed.

  Furthermore, the composition of the present invention is a mode other than the TN type, that is, a high twist angle STN type liquid crystal electro-optical element, a guest-host (GH) type liquid crystal electro-optical element using a pleochroic dye, In-plane switching (IPS) type liquid crystal electro-optical element that drives liquid crystal molecules parallel to the substrate by a direction electric field, VA type liquid crystal electro-optical element that aligns liquid crystal molecules perpendicularly to the substrate, ferroelectric liquid crystal electro-optic It can be used in various ways such as an element. Further, it can be used not only in a method of electrically writing but also in a method of writing by heat.

Hereinafter, the present invention will be described more specifically with reference to examples. The following examples are intended to illustrate the present invention without limiting the present invention.

Example 1
Synthesis of compound (1A)
Under a nitrogen stream, 3.75 g of ground magnesium was suspended in 7.5 ml of THF, and 3.06 g of EtBr was added dropwise. After confirming the exotherm, 34.29 g of the compound (2A) was suspended in 45 ml of THF at 40 ° C., dropped and stirred for 1 hour, and then stirred overnight at room temperature.
The obtained reaction solution was added dropwise to a place where 30.00 g of compound (3A) and 30 ml of THF were cooled to −20 ° C., gradually warmed to room temperature, and stirred for 1 hour. The mixture was treated with 60 ml of 10% hydrochloric acid, and the organic phase was extracted with hexane and washed with 5% aqueous sodium bicarbonate solution and water. After drying, the resulting crude oil was purified by silica chromatography (developing solvent: hexane) and then recrystallized from hexane / solmix to obtain 4.21 g of compound (1A).

The NMR, phase series, and GC-MS of the obtained compound (1A) are shown below.
<NMR>
¹⁹ F-NMR (282.6 MHz, heavy solvent CDCl ₃ , reference CFCl ₃ ) δ (ppm): −78.36 (m, 2F), −117.76 (m, 2F), −132.55 (m, 2F), -163.08 (m, 1F), -210.09 (m, 1F).
¹ H-NMR (282.6 MHz, heavy solvent CDCl ₃ , reference SiMe ₄ ) δ (ppm): 6.84 (m, 2H), 4.80 (m, 1H), 2.0-0.7 (br 27H).
<Phase series>
C 20 ° C. Sm 58.5 ° C. N 106.9I (C: crystal, Sm: smectic, N: nematic phase, I: isotropic phase)
<GC-MS>
m / z = 486

  Moreover, the following physical property was measured about the compound (1A) using liquid crystal composition ZLI-4792 by Merck as a mother liquid crystal. The results are shown in Table 1.

[Clear point]
Using a mixture of 30% by mass of compound (1A) and 70% by mass of mother liquid crystals, a sample (target compound and mother liquid crystals) was placed on a hot plate (Mettler FP-82HT type hot stage) of a melting point measuring apparatus equipped with a polarizing microscope. And a polarizing microscope was observed while heating at a rate of 1 ° C./min. The temperature at which a part of the sample was changed from the liquid crystal phase to the isotropic liquid was 77.8 ° C. as a clearing point (Tc) and was obtained by extrapolation.
[Measurement of refractive index anisotropy (Δn)]
Using a mixture of 30% by mass of compound (1A) and 70% by mass of base liquid crystal, the refractive index anisotropy (Δn) at 25 ° C. was determined by extrapolation.

[Measurement of dielectric anisotropy (Δε)]
A mixture of 10% by mass of the compound (1A) and 90% by mass of the base liquid crystal was sealed between two glass cells (interval of 8 μm). A voltage of 100 mV was applied to the cell, and the dielectric constant (ε _⊥ ) in the minor axis direction of the liquid crystal molecules was measured. A voltage of 88 V was applied to measure the dielectric constant (ε _‖ ) in the major axis direction of the liquid crystal molecules.
Dielectric anisotropy of the compound ([Delta] [epsilon]) is seeking [Delta] [epsilon] of the composition from the equation [Delta] [epsilon] = epsilon _{‖-epsilon ⊥,} was determined by extrapolation.
When Δε at 20 ° C. was determined, it was 9.38.

[Measurement of bulk viscosity]
A liquid crystal composition comprising 70% by weight of the mother liquid crystal and 30% by weight of the compound (1A) was prepared, measured at 25 ° C. and 0 ° C. using a shear viscometer, and calculated by extrapolation. 82mm ² · s ^-1, was 78.77mm ² · s ^-1 at 0 ° C..

(Comparative Example 1)
It was 73.3 degreeC when Tc of the compound of the comparative example 1 was calculated | required by the method similar to a compound (1A) by the extrapolation method.
From this, it was found that a liquid crystal compound having a linking chain of —CF ₂ CHFCF ₂ O— exhibits a higher Tc than that of a single bond.

(Comparative Example 2)
It was 8.15 when (DELTA) epsilon of the compound of the comparative example 2 was calculated | required by the method similar to the compound of a compound (1A) by the extrapolation method.
From this, it was found that a liquid crystal compound having a linking chain of —CF ₂ CHFCF ₂ O— exhibits a larger absolute value Δε than that of —CH ₂ CH ₂ CF ₂ O—.

As described above, it has been found that the fluorine-containing liquid crystal compound of the present invention has sufficient values for the viscosity, Δε, Tc, and Δn to be used as components of the liquid crystal composition.
It has been clarified that by using such a compound of the present invention for a liquid crystal composition, compositions having various performances required for a liquid crystal electro-optical element can be prepared.

Based on Example 1 and the scheme described above, the following compounds can be prepared. In the following formulae, -Cy- and -Ph- are the same as described above, and other symbols have the following meanings.
-Ph (2F)-: 2-fluoro-1,4-phenylene group-Ph (2F, 6F)-: 2,6-difluoro-1,4-phenylene group-Ph (2F, 3F)-: 2,3 -Difluoro-1,4-phenylene group Moreover, the substitution position of the substituted ring group corresponding to A ^{1 to} A ⁷ in the formula (1) is always the 4-position when the ring member carbon is closer to R ¹ , R ² This is equivalent to the case where the one close to is always the first place.

  Examples of the bicyclic compound (where all of a to e are 0) include the following.

C ₃ H ₇ -Ph-CF ₂ CHFCF ₂ O-Ph-C ₂ H ₅
C ₃ H ₇ -Ph-CF ₂ CHFCF ₂ O-Ph-F
C ₃ H ₇ -Ph-CF ₂ CHFCF ₂ O-Ph (2F) -F
C ₃ H ₇ -Ph-CF ₂ CHFCF ₂ O-Ph (2F, 6F) -F
C ₃ H ₇ -Ph-CF ₂ CHFCF ₂ O-Ph (2F, 6F) -CN
C ₃ H ₇ -Ph-CF ₂ CHFCF ₂ O-Ph (2F, 6F) -NCS
C ₃ H ₇ -Ph-CF ₂ CHFCF ₂ O-Ph (2F, 6F) -SF ₅
C ₃ H ₇ -Ph-CF ₂ CHFCF ₂ O-Ph (2F) -OCF ₃
C ₃ H ₇ O-Ph-CF ₂ CHFCF ₂ O-Ph (2F) -OCF ₃
C ₂ H ₅ -Ph-CF ₂ CHFCF ₂ O-Ph (2F, 3F) -OCH ₃
C ₅ H ₁₁ -Ph-CF ₂ CHFCF ₂ O-Ph (2F, 6F) -OCF ₂ H
CH ₃ CH = CH-C ₂ H ₄ -Ph-CF ₂ CHFCF ₂ O-Ph (2F, 6F) -F
CH ₃ OCH ₂ -Ph-CF ₂ CHFCF ₂ O-Ph (2F, 3F) -F
C ₃ H ₇ O-Ph (2F, 3F) -CF ₂ CHFCF ₂ O-Ph (2F, 3F) -F

C ₃ H ₇ -Cy-CF ₂ CHFCF ₂ O-Ph-C ₂ H ₅
C ₃ H ₇ -Cy-CF ₂ CHFCF ₂ O-Ph (2F, 6F) -F
C ₃ H ₇ -Cy-CF ₂ CHFCF ₂ O-Ph (2F, 6F) -CN
C ₃ H ₇ O-Cy-CF ₂ CHFCF ₂ O-Ph (2F) -OCF ₃
C ₂ H ₅ -Cy-CF ₂ CHFCF ₂ O-Ph (2F, 3F) -OCH ₃
CH ₃ CH = CH-C ₂ H ₄ -Cy-CF ₂ CHFCF ₂ O-Ph (2F, 6F) -F
CH ₂ = CH-Cy-CF ₂ CHFCF ₂ O-Ph (2F, 6F) -F
C ₅ H ₁₁ -Cy-CF ₂ CHFCF ₂ O-Ph (2F, 6F) -OCF ₂ H

  Examples of the tricyclic compound (one in which any one of a to e is 1 and the other 3 are 0) include the following.

C ₃ H ₇ -Cy-Ph-CF ₂ CHFCF ₂ O-Ph-C ₂ H ₅
C ₃ H ₇ -Cy-Ph-CF ₂ CHFCF ₂ O-Ph-F
C ₃ H ₇ -Cy-Ph-CF ₂ CHFCF ₂ O-Ph (2F) -F
C ₃ H ₇ -Cy-Ph-CF ₂ CHFCF ₂ O-Ph (2F, 6F) -F
C ₃ H ₇ -Cy-Ph-CF ₂ CHFCF ₂ O-Ph (2F, 6F) -CN
C ₂ H ₅ -Cy-Ph-CF ₂ CHFCF ₂ O-Ph (2F, 6F) -NCS
C ₃ H ₇ -Cy-Ph-CF ₂ CHFCF ₂ O-Ph (2F, 6F) -SF ₅
C ₅ H ₁₁ -Cy-Ph-CF ₂ CHFCF ₂ O-Ph (2F, 6F) -OCF ₃
C ₃ H ₇ -Cy-Ph-CF ₂ CHFCF ₂ O-Ph (2F, 3F) -OC ₂ H ₅
C ₂ H ₅ -Cy-Ph (2F, 3F) -CF ₂ CHFCF ₂ O-Ph (2F, 3F) -OC ₂ H ₅
C ₃ H ₇ -Cy-Ph (2F) -CF ₂ CHFCF ₂ O-Ph (2F, 6F) -F
C ₃ H ₇ -Cy-Ph (2F, 6F) -CF ₂ CHFCF ₂ O-Ph (2F, 6F) -F
C ₃ H ₇ -Cy-Ph (2F, 6F) -CF ₂ CHFCF ₂ O-Ph (2F, 6F) -OCF ₃
C ₃ H ₇ -Cy-Ph (2F, 6F) -CF2CHFCF ₂ O-Ph (2F, 6F) -CN

C ₂ H ₅ -Ph-Ph-CF ₂ CHFCF ₂ O-Ph-F
C ₃ H ₇ -Ph-Ph-CF ₂ CHFCF ₂ O-Ph (2F) -F
C ₃ H ₇ -Ph-Ph-CF ₂ CHFCF ₂ O-Ph (2F, 6F) -F
_{C 5 H 11 -Ph-Ph-} CF 2 CHFCF 2 O-Ph (2F, 6F) -CN
C ₃ H ₇ -Ph-Ph-CF ₂ CHFCF ₂ O-Ph (2F, 6F) -NCS
C ₃ H ₇ -Ph-Ph-CF ₂ CHFCF ₂ O-Ph (2F, 6F) -SF ₅
C ₃ H ₇ -Ph-Ph-CF ₂ CHFCF ₂ O-Ph (2F, 6F) -OCF ₃
C ₂ H ₅ -Ph-Ph-CF ₂ CHFCF ₂ O-Ph (2F, 3F) -OC ₂ H ₅
C ₃ H ₇ -Ph-Ph (2F, 3F) -CF ₂ CHFCF ₂ O-Ph (2F, 3F) -OC ₂ H ₅
C ₃ H ₇ -Ph-Ph (2F) -CF ₂ CHFCF ₂ O-Ph (2F, 6F) -F
C ₅ H ₁₁ -Ph-Ph (2F, 6F) -CF ₂ CHFCF ₂ O-Ph (2F, 6F) -F

C ₃ H ₇ -Cy-Cy-CF ₂ CHFCF ₂ O-Ph-F
_{CH 2 = CH-Cy-Cy} -CF 2 CHFCF 2 O-Ph (2F) -F
C ₃ H ₇ -Cy-Cy-CF ₂ CHFCF ₂ O-Ph (2F) -OCF ₃
C ₃ H ₇ -Cy-Cy-CF ₂ CHFCF ₂ O-Ph (2F, 6F) -F
C ₃ H ₇ -Cy-Cy-CF ₂ CHFCF ₂ O-Ph (2F, 6F) -CN
C ₅ H ₁₁ -Cy-Cy-CF ₂ CHFCF ₂ O-Ph (2F, 3F) -OC ₂ H ₅
C ₅ H ₁₁ -Cy-Cy-CF ₂ CHFCF ₂ O-Ph (2F, 6F) -OCF ₂ H

C ₂ H ₅ -Ph-CF ₂ CHFCF ₂ O-Ph-Ph (2F) -F
C ₃ H ₇ -Ph-CF ₂ CHFCF ₂ O-Ph-Ph (2F, 6F) -F
C ₃ H ₇ -Ph-CF ₂ CHFCF ₂ O-Ph (2F, 6F) -Ph (2F, 6F) -F
C ₅ H ₁₁ -Ph-CF ₂ CHFCF ₂ O-Ph (2F, 6F) -Ph (2F, 6F) -CN
CH ₃ CH = CHC ₂ H ₄ -Ph-CF ₂ CHFCF ₂ O-Ph-Ph (2F) -F
C ₃ H ₇ -Ph-CF ₂ CHFCF ₂ O-Ph-Ph (2F, 3F) -OCH ₃
C ₃ H ₇ -Ph (2F) -CF ₂ CHFCF ₂ O-Ph-Ph (2F, 6F) -F
C ₂ H ₅ -Ph-CF ₂ CHFCF ₂ O-Ph-Cy-C ₅ H ₁₁
C ₂ H ₅ -Ph-CF ₂ CHFCF ₂ O-Ph (2F) -Cy-C ₅ H ₁₁
C ₃ H ₇ -Ph-CF ₂ CHFCF ₂ O-Ph (2F, 6F) -Cy-C ₅ H ₁₁
C ₃ H ₇ -Ph (2F, 3F) -CF ₂ CHFCF ₂ O-Ph-Cy-OC ₂ H ₅
C ₂ H ₅ -Cy-CF ₂ CHFCF ₂ O-Ph-Ph (2F) -F
C ₅ H ₁₁ -Cy-CF ₂ CHFCF ₂ O-Ph-Ph (2F, 6F) -F
C ₃ H ₇ -Cy-CF ₂ CHFCF ₂ O-Ph (2F, 6F) -Ph (2F) -OCF ₃
C ₃ H ₇ -Cy-CF ₂ CHFCF ₂ O-Ph (2F, 6F) -Ph (2F, 6F) -F
C ₅ H ₁₁ -Cy-CF ₂ CHFCF ₂ O-Ph (2F, 6F) -Ph (2F, 6F) -CN
C ₃ H ₇ -Cy-CF ₂ CHFCF ₂ O-Ph-Ph (2F, 3F) -OC ₂ H ₅

C ₃ H ₇ -Cy-C ₂ H ₄ -Ph-CF ₂ CHFCF ₂ O-Ph (2F) -F
C ₃ H ₇ -Cy-C ₂ H ₄ -Ph (2F) -CF ₂ CHFCF ₂ O-Ph (2F, 6F) -F
C ₃ H ₇ -Cy-C ₂ H ₄ -Ph (2F) -CF ₂ CHFCF ₂ O-Ph (2F, 6F) -OCF ₃
CH ₃ CH = CHC ₂ H ₄ -Cy-C ₂ H ₄ -Ph-CF ₂ CHFCF ₂ O-Ph (2F) -C ₃ H ₇
CH ₂ = CH-Cy-CH ₂ O-Ph-CF ₂ CHFCF ₂ O-Ph (2F) -F
C ₃ H ₇ -Cy-CH ₂ O-Ph (2F, 3F) -CF ₂ CHFCF ₂ O-Ph (2F, 3F) -OC ₂ H ₅

  Examples of the tetracyclic compound (one in which any two of a to e are 1 and the other two are 0) include the following.

C ₃ H ₇ -Ph-CF ₂ CHFCF ₂ O-Ph-Ph-Ph-C ₂ H ₅
C ₃ H ₇ -Ph-CF ₂ CHFCF ₂ O-Ph-Ph-Ph (2F, 6F) -F
C ₂ H ₅ -Ph-CF ₂ CHFCF ₂ O-Ph-Ph (2F, 6F) -Ph (2F) -F
C ₅ H ₁₁ -Ph-CF ₂ CHFCF ₂ O-Ph (2F) -Ph (2F) -Ph (2F) -CN
C ₅ H ₁₁ -Ph-CF ₂ CHFCF ₂ O-Ph (2F) -Ph (2F, 6F) -Ph (2F) -OCF ₃
C ₃ H ₇ -Ph-CF ₂ CHFCF ₂ O-Ph (2F, 6F) -Ph (2F, 6F) -Ph (2F, 6F) -F
C ₂ H ₅ -Ph (2F) -CF ₂ CHFCF ₂ O-Ph-Ph (2F, 6F) -Ph (2F) -CN
C ₂ H ₅ -Ph (2F, 3F) -CF ₂ CHFCF ₂ O-Ph-Ph-Ph (2F) -F

C ₃ H ₇ -Cy-CF ₂ CHFCF ₂ O-Ph-Ph-Ph-C ₂ H ₅
C ₃ H ₇ -Cy-CF ₂ CHFCF ₂ O-Ph-Ph-Ph (2F, 6F) -F
C ₂ H ₅ -Cy-CF ₂ CHFCF ₂ O-Ph-Ph (2F, 3F) -Ph (2F, 3F) -OC ₂ H ₅
C ₅ H ₁₁ -Cy-CF ₂ CHFCF ₂ O-Ph (2F) -Ph (2F) -Ph (2F) -CN
C ₅ H ₁₁ -Cy-CF ₂ CHFCF ₂ O-Ph (2F) -Ph (2F, 6F) -Ph (2F) -OCF ₃
C ₃ H ₇ -Cy-CF ₂ CHFCF ₂ O-Ph (2F, 6F) -Ph (2F, 6F) -Ph (2F, 6F) -F
C ₂ H ₅ -Cy-CF ₂ CHFCF ₂ O-Ph-Ph (2F, 6F) -Ph (2F) -CN

C ₃ H ₇ -Ph-CF ₂ CHFCF ₂ O-Ph (2F, 3F) -Ph (2F, 3F) -Cy-C ₂ H ₅
C ₃ H ₇ -Ph-CF ₂ CHFCF ₂ O-Ph (2F, 6F) -Ph (2F, 6F) -Cy-CH = CH ₂
C ₃ H ₇ -Ph (2F, 3F) -CF ₂ CHFCF ₂ O-Ph (2F, 3F) -Ph (2F, 3F) -Cy-CH ₃
C ₃ H ₇ -Ph-CF ₂ CHFCF ₂ O-Ph (2F, 3F) -Cy-Cy-C ₂ H ₅
C ₃ H ₇ -Ph-CF ₂ CHFCF ₂ O-Ph (2F, 6F) -Cy-Cy-OCH ₃

C ₃ H ₇ -Cy-Ph-CF ₂ CHFCF ₂ O-Ph-Ph-C ₂ H ₅
C ₃ H ₇ -Cy-Ph-CF ₂ CHFCF ₂ O-Ph (2F) -Ph (2F, 6F) -F
C ₅ H ₁₁ -Cy-Ph-CF ₂ CHFCF ₂ O-Ph (2F, 6F) -Ph (2F, 6F) -OCF ₃
C ₃ H ₇ -Cy-Ph-CF ₂ CHFCF ₂ O-Ph-Cy-CH = CH ₂
C ₅ H ₁₁ -Cy-Ph-CF ₂ CHFCF ₂ O-Ph (2F, 3F) -Cy-C ₂ H ₅
C ₃ H ₇ -Cy-Ph (2F, 3F) -CF ₂ CHFCF ₂ O-Ph (2F, 3F) -Cy-C ₂ H ₅
C ₃ H ₇ -Cy-Cy-CF ₂ CHFCF ₂ O-Ph-Ph (2F) -F
C ₅ H ₁₁ -Cy-Cy-CF ₂ CHFCF ₂ O-Ph (2F) -Ph (2F, 6F) -CN
C ₅ H ₁₁ -Cy-Cy-CF ₂ CHFCF ₂ O-Ph (2F, 3F) -Ph (2F, 3F) -OC ₂ H ₅
C ₅ H ₁₁ -Cy-Cy-CF ₂ CHFCF ₂ O-Ph (2F) -Cy-C ₃ H ₇
C ₃ H ₇ -Cy-Cy-CF ₂ CHFCF ₂ O-Ph (2F, 6F) -Cy-OC ₂ H ₅
C ₃ H ₇ -Cy-Cy-CF ₂ CHFCF ₂ O-Ph (2F, 3F) -Cy-OCH ₃

C ₃ H ₇ -Ph-Ph-Ph-CF ₂ CHFCF ₂ O-Ph (2F) -OCF ₃
C ₃ H ₇ -Ph-Ph-Ph (2F, 6F) -CF ₂ CHFCF ₂ O-Ph (2F, 6F) -F
C ₃ H ₇ -Ph-Ph (2F) -Ph (2F, 6F) -CF ₂ CHFCF ₂ O-Ph (2F, 6F) -CN
C ₂ H ₅ -Ph-Ph (2F, 6F) -Ph-CF ₂ CHFCF ₂ O-Ph (2F) -CN
CH ₃ -CH = CH-C ₂ H ₄ -Ph-Ph-Ph-CF ₂ CHFCF ₂ O-Ph (2F) -F
CH ₂ = CH-Cy-Cy-Cy-CF ₂ CHFCF ₂ O-Ph (2F) -OCF ₃
C ₃ H ₇ -Cy-Cy-Cy-CF ₂ CHFCF ₂ O-Ph (2F, 6F) -F
C ₃ H ₇ -Cy-Cy-Cy-CF ₂ CHFCF ₂ O-Ph (2F, 3F) -OC ₂ H ₅
C ₂ H ₅ O-Cy-Cy-Ph-CF ₂ CHFCF ₂ O-Ph (2F) -OCF ₃
C ₃ H ₇ -Cy-Cy-Ph-CF ₂ CHFCF ₂ O-Ph (2F, 6F) -F
C ₃ H ₇ -Cy-Cy-Ph (2F) -CF ₂ CHFCF ₂ O-Ph (2F, 6F) -CN
C ₃ H ₇ -Cy-Cy-Ph-CF ₂ CHFCF ₂ O-Ph (2F, 3F) -OC ₂ H ₅
C ₃ H ₇ -Cy-Ph-Ph-CF ₂ CHFCF ₂ O-Ph (2F) -OCF ₃
C ₃ H ₇ -Cy-Ph-Ph (2F, 6F) -CF ₂ CHFCF ₂ O-Ph (2F, 6F) -F
C ₃ H ₇ -Cy-Ph (2F) -Ph (2F, 6F) -CF ₂ CHFCF ₂ O-Ph (2F, 6F) -CN
C ₂ H ₅ -Cy-Ph (2F, 6F) -Ph-CF ₂ CHFCF ₂ O-Ph (2F) -CN
CH ₂ = CH-Cy-Ph-Ph-CF ₂ CHFCF ₂ O-Ph (2F) -F

  Examples of the pentacyclic compound (one in which any three of a to e are 1 and the other two are 0) include the following.

C ₃ H ₇ -Ph-Ph-Ph-Ph-CF ₂ CHFCF ₂ O-Ph (2F) -F
C ₃ H ₇ -Ph-Ph-Ph-Ph (2F, 6F) -CF ₂ CHFCF ₂ O-Ph (2F, 6F) -F
C ₃ H ₇ -Ph-Ph-Ph (2F) -Ph (2F, 6F) -CF ₂ CHFCF ₂ O-Ph (2F, 6F) -CN
C ₂ H ₅ -Ph-Ph-Ph (2F, 6F) -Ph-CF ₂ CHFCF ₂ O-Ph (2F) -CN
_{CH 3 -CH = CH-C 2} H 4 -Ph-Ph-Ph-Ph-CF 2 CHFCF 2 O-Ph (2F) -F
CH ₂ = CH-Cy-Cy-Cy-Ph-CF ₂ CHFCF ₂ O-Ph (2F) -OCF ₃
C ₃ H ₇ -Cy-Cy-Cy-Ph-CF ₂ CHFCF ₂ O-Ph (2F, 6F) -F
C ₃ H ₇ -Cy-Cy-Cy-Ph-CF ₂ CHFCF ₂ O-Ph (2F, 3F) -OC ₂ H ₅
C ₂ H ₅ O-Cy-Cy-Ph-Ph-CF ₂ CHFCF ₂ O-Ph (2F) -OCF ₃
C ₃ H ₇ -Cy-Cy-Ph-Ph-CF ₂ CHFCF ₂ O-Ph (2F, 6F) -F
C ₃ H ₇ -Cy-Cy-Ph-Ph (2F) -CF ₂ CHFCF ₂ O-Ph (2F, 6F) -CN
C ₃ H ₇ -Cy-Cy-Ph-Ph-CF ₂ CHFCF ₂ O-Ph (2F, 3F) -OC ₂ H ₅
C ₃ H ₇ -Cy-Ph-Ph-Ph-CF ₂ CHFCF ₂ O-Ph (2F) -OCF ₃
C ₃ H ₇ -Cy-Ph-Ph-Ph (2F, 6F) -CF ₂ CHFCF ₂ O-Ph (2F, 6F) -F
C ₃ H ₇ -Cy-Ph-Ph (2F) -Ph (2F, 6F) -CF ₂ CHFCF ₂ O-Ph (2F, 6F) -CN
C ₂ H ₅ -Cy-Ph-Ph (2F, 6F) -Ph-CF ₂ CHFCF ₂ O-Ph (2F) -CN
C ₃ H ₇ -Cy-Ph-Ph-Ph-CF ₂ CHFCF ₂ O-Ph (2F, 6F) -F
CH ₂ = CH-Cy-Ph-Ph-Ph-CF ₂ CHFCF ₂ O-Ph (2F) -F

C ₃ H ₇ -Ph-Ph-Ph-CF2CHFCF ₂ O-Ph-Ph (2F) -F
C ₃ H ₇ -Ph-Ph-Ph (2F, 6F) -CF ₂ CHFCF ₂ O-Ph-Ph (2F, 6F) -F
C ₃ H ₇ -Ph-Ph (2F) -Ph (2F, 6F) -CF ₂ CHFCF ₂ O-Ph-Ph (2F, 6F) -CN
C ₂ H ₅ -Ph-Ph (2F, 6F) -Ph-CF ₂ CHFCF ₂ O-Ph-Ph (2F) -CN
CH ₃ -CH = CH-C ₂ H ₄ -Ph-Ph-Ph-CF ₂ CHFCF ₂ O-Ph-Ph (2F) -F
CH ₂ = CH-Cy-Cy-Cy-CF ₂ CHFCF ₂ O-Ph-Ph (2F) -OCF ₃
C ₃ H ₇ -Cy-Cy-Cy-CF ₂ CHFCF ₂ O-Ph-Ph (2F, 6F) -F
C ₃ H ₇ -Cy-Cy-Cy-CF ₂ CHFCF ₂ O-Ph-Ph (2F, 3F) -OC ₂ H ₅
C ₂ H ₅ O-Cy-Cy-Ph-CF ₂ CHFCF ₂ O-Ph-Ph (2F) -OCF ₃
C ₃ H ₇ -Cy-Cy-Ph-CF ₂ CHFCF ₂ O-Ph-Ph (2F, 6F) -F
C ₃ H ₇ -Cy-Cy-Ph (2F) -CF ₂ CHFCF ₂ O-Ph-Ph (2F, 6F) -CN
C ₃ H ₇ -Cy-Cy-Ph-CF ₂ CHFCF ₂ O-Ph-Ph (2F, 3F) -OC ₂ H ₅
C ₃ H ₇ -Cy-Ph-Ph-CF ₂ CHFCF ₂ O-Ph-Ph (2F) -OCF ₃
C ₃ H ₇ -Cy-Ph-Ph (2F, 6F) -CF ₂ CHFCF ₂ O-Ph-Ph (2F, 6F) -F
C ₃ H ₇ -Cy-Ph (2F) -Ph (2F, 6F) -CF ₂ CHFCF ₂ O-Ph-Ph (2F, 6F) -CN
C ₂ H ₅ -Cy-Ph (2F, 6F) -Ph-CF ₂ CHFCF ₂ O-Ph-Ph (2F) -CN
C ₃ H ₇ -Cy-Ph-Ph-CF ₂ CHFCF ₂ O-Ph-Ph (2F, 6F) -F
CH ₂ = CH-Cy-Ph-Ph-CF ₂ CHFCF ₂ O-Ph-Ph (2F) -F

C ₃ H ₇ -Ph-Ph-CF ₂ CHFCF ₂ O-Ph-Ph-Ph (2F) -F
C ₃ H ₇ -Ph-Ph (2F, 6F) -CF ₂ CHFCF ₂ O-Ph-Ph-Ph (2F, 6F) -F
C ₃ H ₇ -Ph (2F) -Ph (2F, 6F) -CF ₂ CHFCF ₂ O-Ph-Ph-Ph (2F, 6F) -CN
C ₂ H ₅ -Ph (2F, 6F) -Ph-CF ₂ CHFCF ₂ O-Ph-Ph-Ph (2F) -CN
CH ₃ -CH = CH-C ₂ H ₄ -Ph-Ph-CF ₂ CHFCF ₂ O-Ph-Ph-Ph (2F) -F
CH ₂ = CH-Cy-Cy-CF ₂ CHFCF ₂ O-Ph-Cy-Ph (2F) -OCF ₃
C ₃ H ₇ -Cy-Cy-CF ₂ CHFCF ₂ O-Ph-Cy-Ph (2F, 6F) -F
C ₃ H ₇ -Cy-Cy-CF ₂ CHFCF ₂ O-Ph-Cy-Ph (2F, 3F) -OC ₂ H ₅
C ₂ H ₅ O-Cy-Cy-CF ₂ CHFCF ₂ O-Ph-Ph-Ph (2F) -OCF ₃
C ₃ H ₇ -Cy-Cy-CF ₂ CHFCF ₂ O-Ph-Ph-Ph (2F, 6F) -F
C ₃ H ₇ -Cy-Cy-CF ₂ CHFCF ₂ O-Ph-Ph (2F) -Ph (2F, 6F) -CN
C ₃ H ₇ -Cy-Cy-CF ₂ CHFCF ₂ O-Ph-Ph-Ph (2F, 3F) -OC ₂ H ₅
C ₃ H ₇ -Cy-Ph-CF ₂ CHFCF ₂ O-Ph-Ph-Ph (2F) -OCF ₃
C ₃ H ₇ -Cy-Ph (2F, 6F) -CF ₂ CHFCF ₂ O-Ph-Ph-Ph (2F, 6F) -F
C ₃ H ₇ -Cy-Ph (2F) -CF ₂ CHFCF ₂ O-Ph-Ph (2F, 6F) -Ph (2F, 6F) -CN
C ₂ H ₅ -Cy-Ph (2F, 6F) -CF ₂ CHFCF ₂ O-Ph-Ph-Ph (2F) -CN
C ₃ H ₇ -Cy-Ph-CF ₂ CHFCF ₂ O-Ph-Ph-Ph (2F, 6F) -F
CH ₂ = CH-Cy-Ph-CF ₂ CHFCF ₂ O-Ph-Ph-Ph (2F) -F

Claims (6)

A liquid crystal compound represented by the following formula (1).
_{^{R 1 - (A 1) a}} -Z 1 - (A 2) b -Z 2 - (A 3) c -Z 3 -A 4 -CF 2 CHFCF 2 O-A 5 -Z 4 - (A 6) d _{^{-Z 5 - (A 7) e}} -R 2 (1)
The symbol in Formula (1) shows the following meanings.
R ¹ and R ^{2 are} each independently a hydrogen atom, a halogen atom, —CN, —NCS, —SF ₅ or a monovalent aliphatic hydrocarbon group having 1 to 18 carbon atoms, and one of the groups more -CH ₂ - may be substituted with an ethereal oxygen atom or a thioether sulfur atom, any hydrogen atom in the group may be substituted with a fluorine atom.
A ¹ , A ² , A ³ , A ⁴ , A ⁵ , A ⁶ , A ⁷ : independently of each other, trans-1,4-cyclohexylene group, 1,4-cyclohexenylene group, 1, 3 -Cyclobutylene group, 1,2-cyclopropylene group, naphthalene-2,6-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, decahydronaphthalene-2,6-diyl group Or 1,4-phenylene group. One or more hydrogen atoms in the group may be substituted with a halogen atom, and one or two ═CH— groups present in the group may be substituted with a nitrogen atom. Two —CH ₂ — groups may be substituted with an etheric oxygen atom or a thioetheric sulfur atom.
Z ¹ , Z ² , Z ³ , Z ⁴ , Z ⁵ : each independently a single bond, a divalent aliphatic hydrocarbon group having 1 to 4 carbon atoms, and one or more —CH in the group ₂ - may be substituted with an ethereal oxygen atom or a thioether sulfur atom, any hydrogen atom in the group may be substituted with a fluorine atom.
a, b, c, d, e: 0 or 1 independently of each other. However, 0 ≦ a + b + c + d + e ≦ 3. The liquid crystal compound according to claim 1, wherein the liquid crystal compound represented by the formula (1) is a compound represented by the following formula (1-1).
_{^{R 11 - (A 11) a}} -Z 11 - (A 21) b -Z 21 - (A 31) c -Z 31 -A 41 -CF 2 CHFCF 2 O-A 51 -Z 41 - (A 61) d _{^{-Z 51 - (A 71) e}} -R 21 (1-1)
The symbols in the formula have the following meanings.
R ¹¹ and R ^{21 are} each independently a hydrogen atom, a fluorine atom, —SF ₅ , an alkyl group having 1 to 18 carbon atoms, or an alkenyl group having 2 to 18 carbon atoms. One or more —CH ₂ — in the group may be substituted with an etheric oxygen atom or a thioetheric sulfur atom, and one or more hydrogen atoms in the group may be substituted with a fluorine atom.
A ¹¹ , A ²¹ , A ³¹ , A ⁴¹ , A ⁵¹ , A ⁶¹ , A ⁷¹ : Independently of each other, a trans-1,4-cyclohexylene group or a 1,4-phenylene group. One or more hydrogen atoms in the group may be substituted with a halogen atom, and one or two ═CH— groups present in the group may be substituted with a nitrogen atom. One —CH ₂ — group may be substituted with an etheric oxygen atom or a thioetheric sulfur atom.
Z ¹¹ , Z ²¹ , Z ³¹ , Z ⁴¹ , Z ^{51 are} each independently a single bond or an alkylene group having 1 to 4 carbon atoms, and one or more —CH ₂ — in the group is an etheric oxygen It may be substituted with an atom, and one or more hydrogen atoms in the group may be substituted with a fluorine atom.
a, b, c, d and e have the same meaning as described above. The liquid crystal compound according to claim 1 or 2, wherein the liquid crystal compound represented by the formula (1) is a compound represented by the following formula (1-2).
_{^{R 12 - (A 12) a}} -Z 12 - (A 22) b -Z 22 - (A 32) c -Z 32 -A 42 -CF 2 CHFCF 2 O-A 52 -Z 42 - (A 62) d _{^{-Z 52 - (A 72) e}} -R 22 (1-2)
The symbols in the formula have the following meanings.
R ¹² : a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or a substituted alkyl group having 1 to 10 carbon atoms.
R ²² : a fluorine atom, —SF ₅ , a hydrogen atom, an alkyl group having 1 to 10 carbon atoms or a substituted alkyl group having 1 to 10 carbon atoms.
A ¹² , A ²² , A ³² , A ⁵² , A ⁶² , A ⁷² : independently of each other, a trans-1,4-cyclohexylene group or a 1,4-phenylene group. One or more hydrogen atoms in the group may be substituted with a halogen atom, and one or two ═CH— groups present in the group may be substituted with a nitrogen atom. One —CH ₂ — group may be substituted with an etheric oxygen atom or a thioetheric sulfur atom.
^A42 : trans-1,4-cyclohexylene group. One or more hydrogen atoms in the group may be substituted with a halogen atom, and one or two —CH ₂ — groups may be substituted with an etheric oxygen atom or a thioetheric sulfur atom.
Z ¹² , Z ²² , Z ³² , Z ⁴² , Z ⁵² : each independently a single bond or an alkylene group having 1 to 4 carbon atoms.
a, b, c, d and e have the same meaning as described above. The method for producing a liquid crystal compound represented by the formula (1) according to claim 1, wherein the compound represented by the following formula (2) is reacted with a compound represented by the following formula (3).
_{^{R 1 - (A 1) a}} -Z 1 - (A 2) b -Z 2 - (A 3) c -Z 3 -A 4 -X (2)
CF ₂ = CFCF ₂ O—A ⁵ —Z ⁴ — (A ⁶ ) _d —Z ⁵ — (A ⁷ ) _e —R ² (3)
R ¹ , R ² , A ¹ , A ² , A ³ , A ⁴ , A ⁵ , A ⁶ , A ⁷ , Z ¹ , Z ² , Z ³ , Z ⁴ , in Formula (2) and Formula (3) Z ⁵ , a, b, c, d and e are as defined in formula (1) in claim 1 and X is a halogen atom.   A liquid crystal composition comprising the liquid crystal compound according to claim 1.   A liquid crystal electro-optical element formed by sealing the liquid crystal composition according to claim 5 between two substrates provided with electrodes.