TW528794B - Naphthalene derivative and liquid crystal composition comprising the same - Google Patents

Abstract

Disclosed is a novel liquid-crystalline compound which is a naphthalene derivative useful as an electro-optical liquid crystal display material, a liquid crystal composition containing such naphthalene derivatives and a liquid crystal display device comprising the same. The naphthalene derivative provided by the present invention exhibits an excellent liquid-crystallinity and miscibility with currently widely used liquid crystal compositions or compositions. The addition of the naphthalene derivative makes it possible to drastically lower the threshold voltage of the liquid crystal composition while maintaining its high response. The naphthalene derivative of the present invention is characterized by a large birefringence index. Further, most of the naphthalene derivative of the present invention has no strongly polar group in its molecule and thus can also be used for active matrix driving. Moreover, as shown in the foregoing examples, the naphthalene derivative of the present invention can be easily produced and is colorless and chemically stable. Accordingly, the liquid crystal composition comprising the naphthalene derivative of the present invention is extremely useful as a practical liquid crystal composition, particularly a liquid crystal composition which can operate within a wide temperature range and requires a high speed response and a low voltage driving.

Description

528794 V. Description of the invention (l) ----- [Technical field to which the invention belongs] The present invention relates to a novel liquid crystal compound belonging to a naphthalene derivative useful as an electro-optical liquid crystal display material and a liquid crystal composition containing the naphthalene derivative. And a liquid crystal display element using the composition. [Prior technology] In addition to being used in clocks and desktop computers, liquid crystal display elements are also used in various measuring instruments, automobile dashboards, word processors, electronic notebooks, printers, computers, televisions, and so on. Typical liquid crystal display methods include TN (twisted nematic) type, STN (super twisted nematic) type, DS (dynamic light scattering) type, GH (encapsulation or cage) type, or possibly High-speed response such as FLC (Ferroelectric Liquid Crystal). In addition, the driving method is also the same, from the known electrostatic driving method to the multiple driving method has been generalized, in addition to the simple matrix method and the recent active matrix method has been put into practical use. For this purpose, liquid crystal materials used in these methods have so far synthesized a large number of liquid crystal compounds, and these compounds are used in accordance with their display mode, driving mode or application. However, the improvement of liquid crystal display elements The requirements for performance (improvement of display quality, enlargement of display shadow, etc.) are increasing year by year, and in order to meet its requirements, the development of novel liquid crystal compounds continues. Liquid crystal compounds are generally composed of a central skeleton portion called a core and two end portions on both sides. Generally, in the structure constituting the core part of a liquid crystal compound, 1,4-phenylene (sometimes substituted with i to 2 halogen atoms, cyano, methyl I, etc.) and trans- 1,4-cyclohexyl Take up most of it. However, a liquid crystal compound composed of only 1,4-phenylene and trans-cyclohexyl is

528794 V. Description of the invention (2) The types or characteristics are also limited. It is true that the above requirements are true. On the day of the attack, the compound has not been able to cope with I 4-phenylene and trans-1-, 4-cyclohexidine-2,5-diyl, pyrimidine_2,5_di / exo =% structure, such as pyridine Heterocyclic systems such as radicals, or trans-decahydro-6, the other two, 'lupin-trans 2,5_dihydronaphthalene-2,6-diyl, bicyclic [22 秦, 6_ —yl, Qin — 2,6 ~ 2 Condensed ring systems such as base, tetra-burned-U-diyl, etc. are also practically used in the 2 octyl V, stilbene, and spiro [W] -heptyl groups. Xuan 'to " previously' only =! Temple ring Γ 'naphthalene-2,6-diyl, although it has been reported for a long time, but its liquid crystal properties (phase transfer port nematic liquid transfer of victory) / 里 度), especially as the most, / 右 Right-Master ^ !, is almost completely undiscovered. (Regarding smectic liquid crystals, the optically active alcoholic acid of ii f formic acid is not an interesting property when it is used as a strong dielectric liquid crystal.) Talents are usually in liquid crystal compounds, and at least one of the terminal portions is a side chain of the chain) and In the case of a so-called p-type liquid crystal whose dielectric anisotropy is positive, it is often the case with a polar group. In the TN or STN display mode, in order to reduce its driving voltage, a so-called strong P-type (positive dielectric anisotropy and large report) compound is required. For this purpose, a compound having a cyano group at the end of the molecule and more than one fluorine atom in the same direction of the molecule is usually used. Regarding naphthalene derivatives, only compounds with a stupid naphthalene skeleton have been reported (GB227 1 771 A-cited document (a)), and there are no descriptions of physical properties or application examples. For p-type compounds that can be used in the above active matrix drive method, only

Page 5 528794 V. Description of the invention (3) -----: Compounds in which the atomic gas group or the fluorocarbon group is a polar group. Regarding naphthalene, only compounds with a stupid naphthalene skeleton are listed in GB22227b (reference document (b)) or (a) above, and it does not disclose examples of applications to the live array method. Liquid crystal compounds are those of naphthalene derivatives, and in general, the compatibility of liquid crystal compounds of toilet beans is poor. In order to improve this compatibility, it is effective to introduce a side substituent (especially a fluorine atom) into the ^ skeleton. In addition, in the case of using the above active matrix method, when a terminal polar group is directly introduced into a naphthalene ring, it is also considered to be effective to use a fluorine atom for substitution. There are several examples of such fluoronaphthalene derivatives in the above (a), but not only their physical properties, or even the manufacturer =, they cannot be identified as actual products. In addition, It is impossible to infer what kind of property value a compound has. Furthermore, no compound having a structure in which a fluoroalkoxy group or a fluoroalkyl group is directly bonded to a naphthalene ring has been found.勹 Wang Wangwang is known that in liquid crystal compounds, alkenyl groups are introduced in place of commonly used alkane: as the side bond part, liquid crystal properties can be improved and viscosity can be reduced. ^: Often: ΐϊ steep mountain improvement And other excellent effects. However, it is often the case that these alkenyl% hexyl rings are directly bonded, and fragrances, especially naphthalene ring compounds have not been reported. Introducing side = like 'A naphthalene derivative having a group such as an alkoxyalkyl group, a fluoroalkyl group, a fluoroalkenyl group, or a fluorocarbon in a side chain has not been reported. In a liquid crystal compound, in addition to a single bond ′ 2 —ethylene (-CH2CH2-), a linker having a core ring structure is also known, and many divalent organic groups are also known.

5. Description of the Invention (4) A single bond or a second bond with 1,2-Dingmeimei; ίnight 2 :: ί the matter of compatibility between the liquid crystal compound and the relative liquid crystal compound 矣^ The point is low and among other living things, it is known to have 1,2-butadiene ^ 9 I. However, naphthalene was not found. 5. The liquid crystalline compound of phenylene still has a liquid crystal compound i 〇CF2_) of monofluoromethyleneoxy (_c _ CF = CF-) or a difluorovinyl group (thank you. Upper stickiness: low and effective for the high-speed response of r too smoke day stomach μ a Qin He organism has not yet been discovered. [Problem to be solved by the present invention] The crystalline compound that the present invention intends to solve is +%% i, And ^, Yu provides a novel liquid product with a naphthalene ring. And k for-a practical liquid crystal group using the compound [means to solve the problem of the corner of the afternoon] Ask Ϊ In order to solve the above problems, the following items were found to be Solve the above Ϊ · General formula (I)

(D shows an alkyl group having 1 to 20 carbon atoms, a radical oxygen group, a radical oxygen group, or 1 to 7 fluorine atoms. However, these groups may be substituted with a carbon atom group 1 to 7 a and b being 0. Or 1 and satisfy a ^ b, 528794 V. Description of the invention (5) Ring A and ring B each independently represent trans 丨, 4-cyclohexyl, which can replace 1,4-phenylene with one or more fluorine atoms Base, pyridin_2, 5 -diyl, pyrimidine-2,5 -diyl, Hou ° -2, 5-diyl, dagen-3, 6-diyl, trans-U-dioxolidine_ 2,5-diyl, transdecaphthalene-2,6-diyl, or tetrahydronaphthalene-2,6-diyl,

La and Lb are individually indicated —Ch2Ch2—, —, ch = cH-, -ch = chch2ch2-, -ch2ch2ch = ch_, _ch (ch3) ch2, -ch2ch (ch3), -CF = CF-, CF20-, -〇cf2—, one C00_, -〇c〇—, one c one, or a single bond 'X1 to X6 each independently represents a hydrogen atom or a fluorine atom, za represents an it atom, a chlorine atom, a trifluorofluorenyloxy group, It can be substituted with alkyl group having 1 to 7 carbon atoms or alkyl group having 1 to 20 carbon atoms with 1 to 7 fluorine atoms, xyloxy group, alkenyl group, alkenyl group, or the general formula (IIa) or (IIb) The base shown by (lla) (lib), in (Ila) or (lib), Lc and Ld each represent a d ch2-, -ch2ch2ch2ch2-, -ch = ch-, -ch = chch2ch2 -, Ch2ch2ch = CH-CH (CH3) CH2, -CH2CH (CH3), -CF: CF-, -CF2〇-, -OCF2-, -COO-, -0C0-, -c = c-, or single The bond, ring C and ring D respectively represent trans 1,4-cyclohexyl, which can be substituted with 1,4-phenylene, cyno-2,5-diyl, and one or more gas atoms. Close-bite-2,5 fluorenyl, Plough-2, 5-diyl, Dagen-3,6-diyl, Trans-1,3-dioxolidine-1 2,5-diyl, Transdecahydronaphthalene -2,6-diyl, or tetralin-2, 6-diyl '

Zb and fluorine atom, chlorine atom, bromine atom, iodine atom, hydrogen atom, cyano, -SCN, -0CN, 0R ', -OR', -0C0R, or -COOR ', and R' represents the number of carbon atoms 1 to 20 carbon or 2 to 2 carbon atoms

528794

Oxygen, these groups may be substituted with alkoxy groups having 1 to 10 carbon atoms, and the group containing alkoxy group, alkoxy group, or alkoxycarbonyl group may also be used. Moreover, 1 ^ contained in these groups is more than 1 ⑴ The substitution of fluorine atom is also possible. It can be generated due to substitution or divergence. It can be optically active when it is called an antiatom or it can be racemized, but with the following conditions: J, 1), za table = (iIa), case b = 〇, in. In the case of (IIb), 仏 〇, where P represents a atom, a chlorine atom, a trifluoromethoxy group, and may be substituted with an alkoxy group having 1 to 7 carbon atoms or a carbon atom having 1 to 7 fluorine atoms. In the case of an alkyl group, an alkoxy group, an alkenyl group, and an alkenyl group of ~ 20, & = 1,

2) In Za (^ Iia), the ring c represents a 4-phenylene group which may be substituted with a fluorine atom, and represents a fluorine atom, a chlorine atom, a trifluoromethoxy group, and an alkyl group which may be substituted with a fluorine atom. In the case of an alkyl or alkoxy group, Lc represents-, -CH = CH- -CH = CHCH2CH2-, CH2CH2CH: CH-, -ch (ch3) ch2, -ch2ch (CH3), -CF = CF-, -CF2 〇-, or -0Cf2 one, and / or at least one of X1 to X6 represents a fluorine atom, 3) in the case of Za representing an alkyl group or an alkoxy group, at least one of fluorine atoms in χ1 to χ6 represents a fluorine atom, And / or Lc means -Ch2Ch2CH CH _CF = CF-, -CF20-, or -〇CF2-,

4) When za represents a fluorine atom or a chlorine atom, La represents a single bond, and ring A represents a 1,4-phenylene group which may be substituted with a gas atom, b = 0 or b = 1, and Lb represents a single bond, 5) When a = b = 0, X1 represents a fluorine atom and χ2 ~ χ6 represent a hydrogen atom, and Lc represents a single bond, Zb represents a fluorine atom, a chlorine atom, a hydrogen atom, a trifluoromethoxy group, an alkenyl group, Alkenyl, cyano, or cyano)

Page 9 528794 V. Description of the invention (7) '---- Naphthalene derivatives shown. 2. The compound according to the above item, in the general formula (1), a = b = 1. 3. The compound according to item 1 above, in the general formula (1), a = 1, b = 〇, and Za is selected from a fluorine atom, a gas atom, and a trifluorofluorenyl group, and may be substituted with a carbon number of 1 to An alkoxy group of 7 or a 1- to 7-fluorine atom having a carbon atom number of i to 20, a fluorenyl group, a hydrazine group, and a dilute oxygen group. 4. The compound according to item 1 above, in the general formula (!) A = l, b and

Za is represented by the general formula (I I a). In the general formula (I), a = b = 〇, and. In the general formula (I), a = b =: 0, and. 5 · The compound according to item 1 above is represented by the general formula (I I a). 6. The compound as described in item 1 above is represented by the general formula (lib). 7. As in the above A-b (I), the compound of La, Lb ic,, 5, or 6 is in the general formula. , L, and Ld are each independently selected from -CH2CH2- or a single bond, and ring A is a compound selected from ^, 3, 4, or 7; in the general formula (I), phenylene 2, Ht4 —Cyclohexyl, phenyl, 2-to- ^. One gas 丨, 4-phenylene, or trans-decahydronaphthalene-2, 6-diyl 9 · As in Shufan 1, ring B is a compound with 1 β 2, 7, or 8 in which the general formula ( I) 10. Those who extend their base. In the above 1, 4, R c,, _, the compounds of ring C and ring η 4 b, 6, or 7 are independently selected from 1,4-phenylene in the general formula (I) Base, 2-fluoro_1 > 4-one, phenylene, 2, 3-difluoro-1, 4-phenylene, or 3, 5- 528794 5. Description of the invention (8) Difluoro-1, 4-- Stretcher.化合物 As for the compound of item 1, 2, 3, 7, 8, or 9 above, the general formula V.L is selected! It can replace the dilute radicals with 1 to 4 atomic atoms and the dilute radicals with 4 to 2 atomic atoms or the dilute oxygenated groups with 3 to 12 carbon atoms. 12. As in the above 1, 2, 3, 7, s, = (Π φ 7a. ^ ^ 8 or 9 compounds, in the general formula, 丄 "Z is distantly replaceable with 1 ~ 7 exhaustion 浯~ Β Λ + ^ ^ Γ An alkyl or alkoxy group having 1 U carbon atoms, which is a solid atom.

Za is a trifluoromethoxy group. Y is a compound as described in item 12 above. In the general formula (I), 14 is as j, 2, 3, 4, 5, and it13 are described in item Λ t4. In the general formula (1), χι is an appearance = person. In the general formula (1), X2 is a fluorine atom of 1. The compound of the second or third item in the original formula (1), in the general formula (1) The general formula is as follows: 1. The liquid crystal composition of item 17 is used to drive the activity matrix. 9. One kind of liquid #; μ is the constituent element. A. Use the liquid crystal of item 17 above. The composition is a liquid crystal :; Seeds: a moving matrix driven liquid crystal element. As described in more detail above, the present invention provides a general formula ⑴, 528794. V. Description of the invention (9)

(D is a novel liquid crystalline compound that belongs to a naphthalene derivative. The alkoxy group of alkoxyalk-7 is more preferably unsubstituted or unsubstituted, or a double bond group. The formula is also preferred. Ra represents an alkyl group, alkyloxy group, alkenyl group, alkenyl group, or alkenyl group with 1 to 20 atomic atoms. These groups may be substituted with a carbon atom or 1 to 7 fluorine atoms. The number of atoms is preferably from 1 to 7. A linear group is preferable, and an alkyl group or an alkenyl group is preferable. An alkyl group is preferably a group or a group substituted with a plurality of fluorine atoms at the terminal, and the group is particularly preferable. The alkenyl group is preferably a saturated 1-alkenyl or 3-alkenyl ring in the ring to which it is directly bonded. The double bond is arranged at the end of the side chain and the stereo configuration is preferably trans. —Butene Or, the fluorene atom directly bonded to its double bond is replaced by a fluorine atom, and A is 3 to ΐΕ) —1-fluoroethenyl, 2,3-difluoroethenyl, 3-fluoro-2-propanyl ^ ^ Monofluoro-2-propenyl, 4-fluoro-3-butenyl, 4 4-fluoro3-butenyl are preferred. Dilute bases are directly combined ~ 3-alkenyl is preferred, 雔 M, $$ clothing is said to be trans-positioned for every occasion where the fragrance is% ": key; 'Put at the end of a side bond or double bond Stereo, wide or = foot: r: 丁 女 ㈣ ^ In a separate table: reverse stretched cyclohexyl, can be replaced with "solid diyl, 咄 哜 -2 ς, _ phenyl, pyridine-2, 5- Diyl, pyrimidine-2, 5- -2, 5-diyl, transdeca = Jing-3, 6-diyl, trans L 3-dioxoline naphthalene 2, 6 monoyl, or tetrahydronaphthalene-1 2, 6-diyl, 528794 V. Description of the invention (ίο) And trans 1,4-cyclohexyl, J, 4-diphenylene-fluoro-1,4-phenylene, 2,3-difluoro _ 丨, 4 two, "its oxo phenyl, 3 phenyl, or transdecahydronaphthalene ~ 2,6_ di I base, 2, 6 ~ difluoro__, 4_ is better, and ring A H is required to be extremely strong p-type. (The ring β is preferably a cyclohexyl ring and 2,6-difluoro-1,4-phenylene. 豕 5 is 2-fluoro-1,4-phenylene anisotropy is negative.) 3_fluoro- 丨, 4 is required to be particularly strong O-type (dielectric phenylene is preferred. 'Base and 2,3-difluoro_ι, 4_

La and Lb are individually indicated— [η —, _CH ^ H ^ H2CH2 '' -ch2ch2ch = ch- ^ -ϋΗαΗκ'Γ2 '' CH = CH ~ ', -CF = CF-, CF2〇-, 〇CF _ (CH3) CH2, -CH2CH (CH3) single bond, which is particularly preferably L, -cf2-, -0C0-, -c ... or 2 'and -ch2cv or single bond. FJ °: Second ,: ★ Single bond is better than that, the fields where at least one and 1 ^ exist are X1 ~ p, respectively. Table 2 is the early bond. f is better. In the case of a compound, where χ1 represents an original fluorine atom, X4 ~ χ6 Α " A, more than one of X ~ X is °, or X1 ~ X3 are both # &疋, χ1 and χ2 both represent fluorine, X4 ~ ρ: non-fluorine atom. When the compound is of the η type, it is preferred that χ1 is fluorine, 个 j is a fluorine atom, or χ1 to χ6 are all hydrogen atoms, and za means "a hydrogen atom." Fluoromethoxy, which can be substituted with a carbon atom, a 7 atom atom, a dead body, and a 70 rutile, alkenyl, alkenyl group with a broken atom number of 1-20, or the general formula (Ila) or (lib) 528794 V. The group shown in the description of the invention (π) includes a fluorine atom, a trifluoromethoxy group, a difluoromethoxy group, a straight-chain alkyl group having 1 to 7 carbon atoms, and a carbon group having 1 to 3 carbon atoms. Straight-bonded oxygen ^, which hinders straight-bonded 3-alkenyl groups with 4 to 7 atoms, straight-bonded ^ alkenyl groups with 3 to 7 carbon atoms ^ alkenyl 'or a base of general formula (I la) or (lib) It is better to use a fluorine atom, trifluoromethoxy'methyl, ethyl, propyl, butyl, pentyl, fluorenyl, ethoxy '3-butenyl, trans 3-pentenyl, aromatic Oxygen, 2-butenyloxy, and radicals of the general formula (II a) are particularly preferred. In (11 &) or (111)), 1 / and 1 / are each represented separately — (: [12 (^ 2 一, — ()] [12 φ ch2ch2civ… CH = CH-, -CH = CHCH2CH2-, CH2CH2CH = CH-,-(CH3) CH2, -CH2CH (CH3), -CF = CF-, -CF20… -OCF ", -COO-, -0C0—, -C Ξ (: one, or single bond, where -CH2CH2-, -CF two CF-, CF20— , -0CF ", or a single bond is preferred, and -CH2CH2- or a single bond is preferred. In addition, when both Le and Ld are present, or when Lc and La are both present, it is preferred that At least one of them is a single bond., And ^ D each independently represents trans 丨, 4-cyclohexyl, which can be substituted with one of: 1,4-fluorine-phenylene, roaring bite-2,5--2 Base, η dense _2, 5- ^, pyren-2, 5-diyl, dagen-3, 6-diyl, trans-h 3-dioxolane, beans ~ diyl, trans-decahydronaphthalene —2, 6-diyl, or tetrahydronaphthalene_2,6-diyl,-* with trans 4-hexylcyclohexyl, which can be substituted with more than one fluorine atom, 4 radicals are preferred, and丨, 4-phenylene, 2-fluoro-1,4-phenylene, 3-fluorophenylene, phenylene, 2,3-difluoro-1,4-phenylene, or 3, 5 -Difluoro_1,4-tertene is more k. Especially when the compound is a P-type compound, 3_fluoro-

Page 14 528794

1,4-phenylene and 3,5-difluoro-1,4-phenylene are more suitable.

Zb and Zc represent a fluorine atom, a chlorine atom, a bromine atom, an iodine group, a cyano group, -SCN, -OCN, OR, -0R,, -〇CDR ,, ^, and lice atom. R: represents a carbon atom number. Alkyl or alkoxy or C :, dilute or alkenyl, these groups may be substituted with 1 to 10 carbon atoms " fluorenyl, fluorenyl, or alkoxycarbonyl, also This atom may be substituted by more than one fluorine atom, because it is optically active or out of place when it replaces the hydrogen-generating asymmetric carbon atom contained in the soil; Zb and Zc are fluorine atoms, chlorine atoms, and hydrogen atoms, and they can be substituted with alkoxy groups having 1 to 7 carbon atoms or alkyl groups having 1 to 20 carbon atoms. Oxy, alkenyl, alkenyloxy, 1-based, or cyano, in which fluorine atom, trifluoromethoxy, digas ^ ""? Two 7 if-bonded 3-alkenyl, straight dialkyl with 3 to 7 carbon atoms Milk group, linear 3-alkenyl with 4 to 7 slaves, 3 to 6 carbon atoms? Straight-bonded fluorenyl 'or cyano is more preferred, and fluorine atom, trifluoromethoxy, methyl, ethyl, propyl, butyl, pentyl, methoxy, ethoxy, 3- Butenyl, trans 3-pentenyl, allyloxy, 2-butenyl, and cyano. , But with the following conditions: 1) When Za represents (Ila)] 3 = 〇, where ^ represents (Iib) a = 〇, where Za represents a fluorine atom, a chlorine atom, a trifluoromethoxy group, but When substituted with an alkoxy group having 1 to 7 carbon atoms or an alkyl group, alkoxy group, alkenyl group, and alkenyl group having 1 to 20 carbon atoms having 1 to 7 fluorine atoms & = 1, 2 ) Represents (Ha) in Za, and ring c represents 1,4-benzyl which may be substituted with a fluorine atom.

Page 15 528794 V. Explanation of the invention (13), and Zb represents a fluorine atom, a chlorine alkyl group or an alkoxy field, a human being, a trifluoromethoxy group, and may be substituted with a fluorine atom CH ...- CH = CHCH2CH2 ~, ΓΗ \ 'LC means-CWH2CH2-, -CH = (CH3), -ChCF-, -CF 〇2 H2CH = CH- -CH (CH3) CH〆-CH2CH,' ^, ^ ^ 2U ~, or -ocf2_, and / or at least one of T1 fluorine atoms in X1 ~ X6, 2 3) Where redundant 3 represents a radical or radical | ^,. For milk-based, at least one of X1 ~ X6 represents fluorine Atom, and / or L. #-^ ^ ORE A Table 7 ^ ~ CH2CH2CH2CH2-, one CF = CF-, -CF2〇—, or —〇cf2- 22 4) Za represents a fluorine atom or a gas atom, La represents a single bond, and ring A In the case of a 1,4-benzyl group which can be substituted with a fluorine atom, b = 0 or b = 1, and Lb represents a single bond, 5) where ab Ο X represents a fluorine atom, and χ 2 to p represent a hydrogen atom, and When the Lc table is a single bond, Zb represents a fluorine atom, a chlorine atom, a fluorene atom, a trifluorofluorenyloxy group, an alkenyl group, an alkenyloxy group, a cyano group, or a cyano group. As described above, the compound of the general formula (I) may include a plurality of compounds, and when classified according to the structure of its core portion, it is preferable to use the compounds of the following ten formulae (la) to (Ie).

Page 16

528794

Page 17 528794

Page 18

528794

Page 528 794

Page 20

528794

Page 21

528794

Page 528794

Page 23

528794

Page 24

528794

Page 528794

Page 26

528794

Page 27

528794

Page 528794

Page 528794

Page 31

528794

Page 32

528794

Page 33

528794

Page 528794

Page 35

528794

Page 36

528794

Page 37

528794 V. Description of Invention (35)

ocf3 ochf2 0CHF2 (leeg) (leei) (leek) (lefa) (lefc) (lefe) (lefg) (lefi) (lefk)

(leeh) (leej) (leem) 0Cfr3 (leef)

(lefh) (lefj) (lefm) In the above formula, R has the same definition as above. R represents a linear alkyl group having 1 to 7 carbon atoms, or a linear alkenyl group having 2 to 7 carbon atoms. Among them, vinyl or 3-butenyl is preferred. Moreover, in the above formula, (iaaa), (Iaad), (Iaae), (Iacb), (iagb), (Uib), (Iana), (Ianb), (land), (Iapa), (iapb ), (Lata), (Iatb), (Iatd), (lava), (Iavb), (iawa), (iawb), (lawd), (laAa), (IaAb), (IaAd), (iaca), (UCb), (IaGa), (IaGb), (IaGd), (IaJa), (iaJb), (IaJd), (IaNa), (IaNb),

Page 38 528794 V. Description of the invention (36) (IaNd), (IaPa), (IaPb), (iapd), (IaTa), (IaTb), (IaTd), (IaVa), (IaVb), (iavd) , (IaZa), (IaZb), (IaZd), (Ibaa), (Ibab), (ibad), (Ibca), (Ibcb), (Ibcd), (Ibea), (Ibeb), (ibed), (ibed), ( (Ibga), (Ibgb), (Ibgd), (Ibia), (Ibib), (ibid), (Ibka), (Ibkb), (Ibkd), (Ibpa), (Ibpb), (ibpd), (Ibsa) (Ibsb), (Ibsd), (Ibta), (Ibtb), (ibtd), (Ibva), (Ibvb), (Ibvd), (Ibxa), (Ibxb), (Ibxd), (Icaa) ~ ( Each compound (Icim), (Idaa) to (Icim) is particularly suitable. The compound (I) of the present invention can be produced by combining the following synthesis methods in the case of R, ring A, ring B, La, and Lb contained in the compound.方法 Method for producing compounds of general formulae (Iaaa) ~ (Ufe) ① Where the target compound is an intermediate of general formula (丨 丨 丨 a) (Ilia) (where Rb represents an alkyl group), the compound is (i ) Make General Formula (IVa)

(In the formula, ^ indicates a halogen atom such as a horse and a bromine atom is preferred, γΓ represents a heart atom, or an iodine atom, etc., a protected group of protected groups, a hydrogen atom, 2? Oxy group, or ¥ oxy group, and other protected organisms and Magnesium is reacted to make :: Naphthalene derivative shown by methoxy group) The naphthalene derivative is made of alkyl lithium such as Grignard reagent, or it can be organically lithiated to make one.

Page 39 528794 V. Description of the invention (37) There is a branch; a metal reagent, and it is made with the general formula (va) (Va) (where Rb represents an alkyl group). 4-Hexanol obtained The derivative is reacted in the presence of an acid, and then dehydrated in the presence of the general formula k to obtain (Via)

(Via) (where Rb represents a thiol group, and ya is defined as the general formula (i-3 naphthalene derivative. It is subjected to contact reduction treatment if necessary; two: i 5) So, the protective group in Bu is Various protective groups such as / oxygen / zirconium are removed and protected with lice bromide, whereby the naphthol derivatives shown in the above can be obtained. Fe C Ila) (11) Make the above obtained in (1) A compound of the formula (Πla) can be reacted with a halogenated alkyl group or a halogenated alkenyl group in the presence of a base to obtain a compound when R in the general formula (lafe) is a calcined group. (I 丨 丨) Make the above (丨) The obtained compound of the general formula (Π I a) is reacted with trifluoromethane yellow wild or digas sulfonium chloride in the presence of a base (such as pyridine, etc.) to obtain the general formula (V11 a).

(In the formula, Rb is defined as an ester. ° Tf (Vila) and T f represents a dipyridite page 8¾ group.)

—. Page 40 528794 V. Description of the invention (38) (iv) Furthermore, in the presence of a nickel catalyst, the general formula (vnia)

Rb —— Ma (villa) (where Rb is defined as before, Ma represents MgBr, MgCl, U, of which MgBr is preferred). An organometallic reagent such as MgBr is reacted to obtain R in the general formula Jaea. Base time compounds. Here, it is a nickel catalyst. Nickel catalysts such as dichloro ^ diphenylphosphine) nickel 氯), dichloro-bis (triphenyllin) ethane] (烧, triphenylphosphine) nickel (〇), etc. (V) The naphthol derivative represented by the general formula (II la) is reacted with carbon disulfide in the presence of a strong base, and then reacted with an alkylating agent to obtain the general formula (IXa)

(IXa) (The definition of Rb in the formula is the same as above, and R "I represents a lower burning group.) Dithiocarbonate vinegar. Here, the preferred strong test is to test metal nitrides (such as sodium chloride, etc.) (E.g., butane, etc.), aminated chains (e.g., isopropylamine, etc.), alcoholates (e.g., potassium third butoxide, etc.), and preferred alkylating agents are panthane, iodoethane, Desert methane, desert ethane, dimethyl sulfate, or methyl p-toluate, etc. The general formula (Iaca) can be obtained by reacting this dithiocarbonate with ions in the presence of a cationic generator. Where R is an alkyl compound. As a halide cation generator, ^ iodosuccinimide (nis), N-bromosuccinimide (NBS), N-chlorosuccinimide (Nc di) Mo-5 5-dimethyl allantoin (H), etc., and as a sharpening source, use two mice: tetrabutylfluoride (TBA ^), hydrogen fluoride ^ ratio. Fixed complex (H / py), or hydrogen fluoride -Melamine complex (HF-mel), etc. 4 ^ ^ inches. In the case of having an aromatic ring 528794 V. Description of the invention (39) " ^--Sometimes, because of halogen ^ ^ In this case, borrow Burning base clock Ding Li makes the fragrant ring toothed. After bellification, it is protonated; Ding Zhong, etc.) Pass the obtained compound through metal ⑺) and let the above ⑴ get: the target compound can be obtained. In the presence of sodium and ammonia When a compound of the general formula (11 Ia) is reacted with hydrogen sulfite, a compound of the general formula (X a) nb Γ ~ \ / — λ (Xa) (wherein Rb is as defined above and J) can be obtained. To a meta-acid salt "Γ ~ \ Jν h melon +: (Xla) (where Rb is defined as an arrow,, and the general formula (I aaa) is obtained =: this makes Dunyuan such as hydrofluoric acid work (vii) The above σ as in (v) above is made of gaseous copper, etc .; to the general formula, ^^ compound, the use of the gas source group of the compound can be obtained in the general formula (Iaba) above Where R is sintered (VI11) to change the naphthol derivative represented by the general formula 变为 to the general formula (XI⑷ K JV y-Λ __ Ο

(Xlla) The thioformic acid shown in (before the definition of Γ) allows it to react with fluoride ions in the presence of d produced by tooth cations (lada) t .R ^ ^ ^ ^ Use N-iodine axis 醯Imine (NIS), Ν_ Mo Hu axis / Τ 醯 醯 胺 imine UCS), or i 3- 1-5 5 a / „S) Ν '" 1, and can be used for fluoride ion source ;: A allantoin (_ etc. Diaoding you 'will use one ^ one ratified tetrabutylammonium (TBAH2f3),

Page 42

528794

5. Description of the invention (40) Hydrogen fluoride ~ pyridine complex (HF-Py), or hydrogen fluoride-melamine complex (HF-mel), etc. In the case where an aromatic sulfonium is possessed, the aromatic ring may be deactivated by the action of a halide. In this case, the obtained compound is lithiated with alkyl lithium (such as butyl lithium), and then protonated.

The compound of interest. In J (1X), the naphthol derivative represented by the general formula (III a) is i-equivalent fluorine t-bistetrafluoroborate N, N, -difluoro_2, 2, -dioxin or N-fluoro The general formula (χ 111 &) can be obtained when the tris-dioxopyridine-2 -sulfonate is fluorinated.

Rb ^ K > ^ 0H (xilla) compounds, and by-products of general formulae (XlVa) and (XVa)

(Wherein Rb is as defined above). (X) the naphthalene compound represented by the general formula (ma) is used to make a chlorotetracarboxylic acid, chloromethyl m4_diazabicyclo [n, an agent such as a tetrafluoroborate, fluoro-4-hydroxy-14- heavy When azabicyclo [2'octane or fluorinated, the formula (XIVa), '2] octane, etc. can be selected.

(XlVa) (wherein Rb is as defined above)-a compound when pyridine or the like is fluorinated. This substance can be obtained by the fluorinating agent '

E.g. DAST or HF

Page 528 794

(XlVa)

A compound (wherein Rb has the same meaning as defined above), and then when this is contact-reduced, a compound in which R in the general formula (laad) is an alkyl group can be obtained. (xi) The compound of general formula (Iaad) obtained according to the above (X) is borrowed from butyl lithium, and after the metal is lithiated, a fluorinating agent such as dichlorotetrafluoroborate chloromethyl_4_fluoro1,4 -When the diazabicyclo [2, 2, 2] octane or difluorotetrafluoroborate buflu_4___1, 4-diazabicyclo [2, 2, 2] octane, etc., act, the above-mentioned formula ( Iaab) Compounds in which R is an alkyl group. (xii) When the compound of the general formula (XIIIa) shown in the above (ix) is converted into a sulfonic acid ester according to the method of (iii), contact reduction may be performed to obtain R in the general formula (Iaab) when the alkyl group is an alkyl group. Of compounds. " " (xiii) After the compound of the general formula (XVa) shown in the above (ix) is changed to the acid g in accordance with the method (Ui), the R in the general formula (Iaag) can be obtained by contact reduction. A compound when it is an alkyl group. (xiv) In the above (vi), the general formula (xVIIa) is used

When the compounds of the formula (where Wa and P are as defined above) are substituted for the humanoids of the general formula (IVa), the compound is passed through the general formula (XVI I la)

(The definition in the formula is the same as before), the general formula (XIXa) can also be obtained.

Page 44 528794 V. Description of the invention (42) (where Rb has the same definition as above) The compound liquid is nitrated, and then this compound can be obtained by reduction of nitric acid and sulfuric acid ^ in general formula (XXa) ) 'Nh2 (XXa) (wherein Rb has the same definition as above). (XV) changing the compound obtained by the above (xiv) to the formula (XXla) ^ (XXa) by nitrite

(XXla) (wherein the definition of Rb is the same as above), the chemical compounds 4 and so on can be used to obtain the 弋 0 mouth). After this, a fluorine source such as hydrofluoric acid μ but N is a compound of formula (laac). (xvi) Acts on the formula (xv) of the formula (xχι) which is served by the above (xv)% pe, s ^ ^, and obtains the radical intact < compound in the formula (Iabc). (xvii) For the above ( xv) The compound of general formula (XXIa) is obtained by reacting water to obtain general formula (XXI Ia)

(XXI la) (wherein Rb is as defined above). (Also: 1 ^) When a compound of the general formula () (111 &) or (乂 ^) or (〇3) is used to perform (ii) ~ (v), (vii), (viii), it can be obtained Formula (Iabb), (Iabd), (iacb), (Iacc), (Iacd), (Iadb), (lade), (Iadd), (iaeb), (Iaec), (Iaed), (Iafb), (( lafc),

Page 45 528794 V. Description of the invention (43) (I a f d) The compound when R is a xyl group. (xix) using general formula (XXIIIa)

(Wa, Ya, X1, X2, and X3 have the same meanings as before) When the compounds of general formula (I Va) are used instead of (i) ~ (vi ii), the general formula (Iaaa) can be obtained. ~ (Iafe) is a compound when R is a radical. ② The target compound is represented by the general formula (I I lb)

When a compound of OH (lllb) (wherein Rc represents an alkyl group) is a bond intermediate. (i) A naphthalene derivative represented by the general formula (IVa) is reacted with magnesium to make a Grignard reagent 'or the naphthalene derivative is organically lithiated with an alkyl lithium such as butyl lithium or the like to make one An organometallic reagent is reacted with a compound represented by the general formula (Vb). If necessary, it is acetalized, and after contact reduction, it is de-acidified to obtain the general formula (XXIVb) (xx_ ( In the formula, the definition of Ya is as described above. The naphthalenecyclohexylcyclohexanone derivative 4 is used. It is related to the general formula (XXVb) CH30 ^ PPh3 (XXVb).

P.46 528794 V. The Wii 11 i g reagent shown in the description of the invention (44) is reacted, followed by hydrolysis with an acid to obtain the general formula (XXVIb)

Cyclohexanecarbonaldehyde derivative shown. Make it the general formula (χχνι Ib) CHr— ^ PPh; 3 WVIIb)

The Wei Wei reagent shown is reacted and then desirably deprotected to obtain a compound when Rb in the general formula (I I I b) is a vinyl group. Furthermore, the compound of the general formula (XXVIb) is reacted with the Weifang reagent of the general formula (xxvb) twice, followed by the reaction with the Weifang reagent of the general formula (XXVIIb), and then the age of Z is deacetylated. The compound in the general formula (111b) when the 3-butenyl group is obtained can be obtained by removing the guarantee. ~ (ii) When the compound represented by general formula (I 丨 丨 b) obtained in (i) of ② is used to perform (i) ~ (viii) of ①, general formula (Iaaa) ~ (Iafe The compound when R is an alkenyl group.方法 Method for producing compounds of general formula (Iaga) ~ (lane) ①The target compound is represented by general formula (I I I e)

(MIc)

Where the compound (wherein R is as defined above) is a bond intermediate. (2) The naphthalene derivative of the general formula = is reacted with magnesium to make a species, a subreagent, =: an acid derivative (the naphthalene derivative of the general formula (iva) can be used as a test compound or an alkyl lithium) Lithium such as butyl lithium, etc.

528794

V. Description of the invention (45) Organometallic reagent, after reacting this substance with trimethylboron and then removing it, boric acid derivative can be obtained), and it is made with the general formula (Vc).

R

The definition of ίΛ " is as before, yb represents a leaving group of a south atom such as a chlorine atom, a bromine atom, or an iodine atom, or a trifluoromethanesulfonyloxy group, among which bromine atom: The benzene derivative shown in) is reacted in the presence of a transition metal catalyst, and the second one can be prepared by removing methoxy from the same. Furthermore, the naphthalene derivative represented by the general formula (Vc) is organolithinated by using a gerenyl reagent or an alkyl lithium such as industrial lithium to prepare an organometallic reagent, and the product is reacted with trimethylboron and then Removal of methyl groups to form boronic acid derivatives, which are then combined with general formula (IVb)

A benzene derivative represented by OH (IVb) (wherein Wb has the same meaning as described above) can be reacted with a transition metal to obtain the desired product. ', Tsai (ii) in (i) of (1) above, the compound of the general formula (nic) is compounded with the compound of the general formula (XVIIa), and the compound of the general formula (IVb) is combined with the general formula (Ivb, ) Milk instead

For the compound (where Wb has the same definition as above), use the same method to formula (XXVII lb) 1 to get 528794

V. Description of Invention (46)

(Wherein R is as defined above). (Hi) In (ii) to (xix) of (1) above, the compound of the general formula (IIIc) is used instead of the compound of the general formula (II la), and the compound of the general formula (XV Illb) is used instead of the general compound. In the case of the compound of the formula (XVI II a), the compound of the general formulae (Iaga) to (Iane) can be obtained by the same method. (3) General formulae (IaGa) ~ (IaMe), (IaZa) ~ (IaZe), (Ibaa) ~

(Ibde) and method for producing compounds of (ibva) to (Ibye) In the above formula, the general formulae (Vd) to (Vg) are used

Rb ~ 0〇

(Ve)

(Vg) (. In the formula, the definition of Rb is the same as above) instead of the compound of general formula (Va), and the general formula (Vd,) ~ (Vg,) (Vd,) (Ve,) 1 = 0 ( Vf) When a compound of (Vg ·) is used instead of a compound of general formula (Vb), the general formulae (IaGa) ~ (IaMe), (IaZa) ~ (iaZe), (Ibaa) ~ (Ibde ), And (Ibva), (Ibye) compounds. ⑷General formula (IaAa) ~ (IaFe), (IaNa) ~ (iaSe), (IaTa) ~

Page 49 528794 V. Description of the invention (47) (IaXe), and (Ibsa) ~ (Ibue) production method of the compound In the above ⑴, the general formula (Vh) ~ (Vk)

Ή0 (Vh) CHO (Vj) DHO (^) (Vk) (where Rb has the same definition as above) to replace the compound of general formula (Va), and the general formula (Vh,) ~ (Vk,) ° When the compound of Tao (w) m OCHho (Vk ,: instead of the compound of general formula (Vb) is used, the general formulae (IaAa) ~ (IaFe), (IaNa) ~ (IaSe), (IaTa) ~ (IaXe), and (Ibsa) ~ (Ibue) compounds. ⑸ general formula (Iana) ~ (Iase), (Iata) ~ (Iaye), (Ibea) ~ (Ibhe), (Ibfa) ~ (Ibme) And a method for producing a compound of (Ibna) to (Ibqe) In the above formula, the general formulae (Vm) to (Vr) (Vm) are used

(Vn) (Vp) (Vq) (Vr)

Page 50 528794, Description of the invention (48) (Formula / R, Yb has the same meaning as above) Instead of the compound of the general formula (Vc) ^ In the same way, the general formula (Iana) ~ (Iase), ( Iata) ~ (Iaye), (Ibea) ~ (Ibhe), (Ibfa) ~ (Ibme), and (Ibna) ~ (Ibqe) compounds. (1) Production method of compound of general formula (Icaa) to (lcch) (1) In the above (丨), when using compound of general formula (Vf) instead of compound of general formula (Va), the same method is used. Can get the general formula (χχιVa)

Of compounds. In addition, in the above (ix), when a compound of the general formula (XXIVa) is used instead of the compound of the general formula (I 11 a), the general formulas (XXVa) and (XXVIa) are obtained in the same manner.

Of compounds. The obtained compounds of the general formulae (XXIVa), (XXVa), and (XXVIa) are reacted with trifluoromethanesulfonic anhydride or trifluoromethanesulfonyl chloride in the presence of a base (such as acetonitrile) to prepare Grade acid ester, in the presence of transition metal catalyst and the following formula (XXVI la)

(In the formula, Rf represents a hydrogen atom, a fluorine atom, a trifluoromethoxy group, a difluoromethoxy group, or a fluorenyl group, and E represents a hydrogen atom or a fluorine atom.) The compound represented by the following formula can be obtained by cross-coupling reaction. (Lcaa) ~ (leaf), (lcba) ~

Page 51 528794 V. Description of the invention (49) (Icbf), (Icca) ~ (iccf), (xXVIIIa and (XXIXa)

OMe (XXVIlla)

(XXIXa) (wherein E has the same meaning as before). After the compound of the general formula (XX v III a) obtained is deprotected by hydrobromic acid, it is reacted with methanesulfonic anhydride or trifluoromethanesulfonyl chloride in the presence of a base (such as pyridine, etc.) to prepare It can be converted into sulfonate and reacted with copper (I) cyanide or reacted with sodium cyanide or potassium cyanide in the presence of f transition metal catalyst to obtain the general formula (Icag), (lcah), (Icbg ), (Icbh), (Iccg), and (lech) compounds. (1) Production method of compounds of general formulae (Icda) to (lceh) (1) In the above formula, when a compound of general formula (Vk) is used instead of a compound of general formula (Vf), a general formula can be obtained by the same method. (Icda) to (Iceh) compounds. (1) Method for producing compounds of formula (Icfa) ~ (Icgh) (i) In the above ⑵, when a compound of general formula (Vp) is used instead of a compound of general formula (vc), (χχχ3 ) (XXXa). Instead of the compound of the general formula (Icgh), a compound of the general formula (xxxa) is used at two m. Fly away I pass formula (Icfa) ~ (Idba) ⑼ general formula (Icha) ~ (Ichm), (icia) ~ (Ici

Page 52 1 ^^ 528794 V. Description of the invention (50) (Idbm), (Idea) ~ (Idem) production method of the compound In the above 使用, the general formula (Vq), (Vr), and (Vs) When a compound of Yb (Vs) is used instead of the compound of general formula (Vp), the general formula (Icha) ~ (Ichm), (Icia) ~ (Icim), (Idba) ~ ( Idbm), (Idea) ~ (Idem) compounds. Production method of compound of general formula (Idba) to (Iefm) In the above formula, general formula (XXVI IB) is used

When a compound of this type is used in place of a compound of general formula (X X V I a), compounds of (Icfa) to (Icgh) can be prepared by the same method. Specific examples of the representative compound (I) of the present invention thus produced are shown in Tables 1 to 3 together with their phase transition temperatures. Table 1 Compounds represented by general formula (lb) R—

No · R- (A) -La- Phase transition temperature (° c) Ib-1 C3H7 _ ^^ y_ Cr48 (N39) I Ib-2 d ^ F Cr 42 I Ib-3 〇3Η7_ ^ ^ C 69 N 142 I Ib-4 WD ~ ° CH3 C 118 N 176 I Page 53 528794 V. Description of the invention (51) χ5χμ / cb Compound represented by general formula (Ic) in Table 2

Enter A Table 3 General formula (I d)

Compound shown

No. Ra_ ^ A) -La- χ4 X2 -Lc- (〇)-^ Phase transition temperature (° c) Ib-1 CsHt ^ Q- Cr99N200. 5 I Ib-2 〇3Ητ-〇- (SK Cr85N198.5 I Ib-3 C2H5 — () — (SK C79 I Ib-4 C3Ht- (3- (SK Cr92.5 N158 I Ib-5 C5H11— (y ~ (SK Cr72. 5 N155.5 I Ib-6 C3Hr ~ 〇 ~ A_ Φ CrllON166 I Ib-7 〇3Η / ~ {Z) ~ Λ_ Crl34. 5N134 I

No. yA X2 -Lc- (c) -Zb Phase transition temperature (° c) Id-1 CaHr- ^ Cr62 I Id-2 C3Hr-^^ ~ άςν Cr50 I Id-3 c3h7-^-^ J0rZH C112 (N78 .5) I Id-4 c3h7- ^ D Cr128 I Id-5 ^ ~ CN Cr109 I Id-6 -〇 ~ F Cr74 (N63) I Id-7 c3h7-^^ Cr-16 N134 I Id-8 C2H5- h ^^ ~ 0ς Cr69. 5 I 52 ^ 794

Cr38 I Cr27.5 I ^ Qkocf3 Cr70SB113 SA119 I ~ ^ -CN Crll3 I, Cr represents a crystalline phase, N represents a nematic phase, and I represents an isotropic liquid (in the table) λ is a compound of the general formula (1) The excellent fruits obtained by adding the liquid crystal composition are described below. ^

Add the compound (Ib — D (lb-1) in Table 1 to a main liquid crystal (Η) at a ratio of 20%

Its temperature range is wide, and it is especially suitable for those with low-viscosity main liquid crystals to prepare a liquid crystal composition (M_〇. As a result, it is known that its liquid temperature is), and the temperature (1 \ _1) is 98.2. (: . This (M —: ^ at 丨 ”its temperature = measured Tn] 'The result is 97 · 8, compared with τ before heating. The heart' / Λ outside line was irradiated for 2 ° hours, the results were not found During standby, after heating, and after UV irradiation

Page 55 528794 V. Description of the invention (60)

, Cyclohexyl benzoate, cyclohexyl derivative, biphenyl derivative, cyclohexyl derivative, bitriphenyl derivative, bicyclohexane derivative, 4-cyclohexyl biphenyl derivative, 4-benzenebicyclohexane derivative Compounds, bitricyclohexane derivatives, 1,2-dicyclohexylethane derivatives, 1,2-diphenylethane derivatives, 1,2-diphenylethane derivatives, (2-cyclohexyl Ethyl) benzene derivatives, 4-phenethylbicyclohexane derivatives, 4- (2-cyclohexylethyl) biphenyl derivatives, and (4-phenyl) cyclohexyl-2 -cyclohexylethane derivatives Compounds, 1- (4-cyclohexylphenyl) -2-phenylacetylene derivatives, phenylpyrimidine derivatives, (4-biphenyl-4-yl) pyrimidine derivatives, phenyl σ ratio σ fixed derivatives , (4-biphenyl-4-yl) roar derivatives. Among these derivatives, biphenyl derivatives, cyclohexyl derivatives, bitriphenyl derivatives, bicyclohexane derivatives, and 4-cyclohexylbiphenyl derivatives are particularly preferred for the application of activity matrix driving. , 4-benzenebicyclohexane derivative, ditricyclohexane derivative, 1,2-dicyclohexylethane derivative, 1,2-diphenylethane derivative, 1,2-diphenylacetylene derivative Compound, (2-cyclohexylethyl) benzene derivative, 4-phenethylbicyclohexane derivative, 4- (2-cyclohexylethyl) biphenyl derivative, 1- (4-phenyl) ring Hexyl-2-cyclohexylethane derivative, 1- (4-cyclohexylphenyl) -2-phenylacetylene derivative. [Example]

Examples of the present invention are described below to further illustrate the present invention. However, the present invention is not limited by these embodiments. The structure of the compound was confirmed by nuclear magnetic resonance (NMR), mass spectrometry (MS), and infrared absorption spectrum (IR). The% of the composition represents WT%. [Example 1] Synthesis of 2- (3,4-difluoro) phenyl-6- (trans 4-propyl) cyclohexylnaphthalene (1-a) 2- (4-propanecyclohex-1-dilute- Synthesis of 1-yl) -6-methoxynaphthalene

Page 63 528794 V. Description of the invention (61) 5.7 g of magnesium is suspended in tetrahydrofuran 2 at a steady reflux temperature at a rate of 6-chun two pairs: 200 ml solution. Next, a solution of tetracycline acid with a concentration of 30 g of tetrahydrosquenching 12000] 1 was added dropwise at room temperature. Borrow toluene 3. 〇 m 丨 γ Take two ::::: ί: water: ί ,,: Γ ° Salt water to wash •, and borrow anhydrous: acid two: flow for 3 hours. Let it cool to room temperature, wash it with water and saturated brine, and dehydrate it with anhydrous sodium sulfate. The solvent was distilled off, and the crystal was recrystallized by ethanol. Cyclohexyl-buten-1-yl) _6_methoxynaphthalene 44 8 Yuji propyl (lb) 2- (trans 4 ~ propylcyclohexyl) -6-methoxynaphthalene In the synthesis, 44.8 g of 2- (4-propanecyclohexyl-butene- 丨 -yl) -6-methoxynaphthalene was dissolved in ethyl acetate 8 0 m 1, and 5% of this was added. Mix at 4 kg / c m2 for 6 hours. The catalyst was filtered off, the solvent was distilled off, and it was dissolved in 180 ml of N, N-dimethylformamide. To this was added 18 g of potassium third butoxide, and the mixture was heated and stirred at 20 ° C for 1 hour. After cooling to room temperature, 70 ml of 10% hydrochloric acid was added thereto, and the deposited crystals were filtered, washed with water, and dried under reduced pressure. 〇g。 Recrystallized by ethanol 'to give 2- (trans4-propanecyclohexyl) -6-methoxynaphthalene 28.0 g. (1-c) Synthesis of 6- (trans4-propanecyclohexyl) -2-naphthol Add 280 ml of acetic acid and 280 ml of 48% hydrobromic acid to 2- (trans 4-propanehexyl) -6-methoxynaphthalene 28 0g while heating under reflux for 12 hours. It was left to cool to room temperature, and water 500 m was added thereto, and the deposited crystals were filtered. After washing with water and drying under reduced pressure, 6_ (trans4-propanecyclohexyl) -2-naphthalene 528794 is obtained. 5. Description of the invention (62) Test 2 6.8 g 〇 (ld) trifluorosulfonate 6- ( Synthesis of trans 4-propanecyclohexyl) methoxynaphthalene-2 -yl

100 ml of dichloromethane and 30 g of trifluorosulfonic anhydride were added to 25.0 g of 6- (trans 4-propanecyclohexyl) -2-naphthol, and the mixture was cooled to 5 ° C. To this was added dropwise a solution of piridin 11. 1 Og in dichloromethane at a rate of not more than 20 ° C. After the dropwise addition is completed, ‘restore the room temperature under a drop’ and add water 150 m 1. The organic layer was washed with water and saturated brine, and then dried over anhydrous sodium sulfate.顾 除> Gui media 'hunting and reducing gel chromatography (solvent is dichloromethane) purification to obtain difluthionite acid 6- (trans 4-propcyclohexyl) oxonaphthyl-2 -yl 36. 7g .

The synthesis of (1-e) 2- (3, 4- monofluoro) phenyl-6- (trans 4-propyl) cyclohexyl naphthalene enables magnesium 1 · Og to be suspended in 2m 1 of tetrahydrofuran, which can be stabilized by tetrahydrofuran 35 ml of a solution of 3,4-difluoro-1-bromobenzene 7.0 g tetrahydrofuran was added dropwise at a rate of reflux. Stir at room temperature! Hours later, the excess magnesium was filtered off, and 6- (trans4-propanecyclohexyl) oxonaphthyl-2-base 10.0 § and triphenylphosphine (triphenylphosphine) were added dropwise at room temperature ( 〇) 0.3 g of tetrahydrofuran 50 ml solution. After stirring for 1 hour at room temperature, 100 ml of water was added. It was extracted with 200 ml of toluene, washed with water and saturated saline, and dried over anhydrous sodium sulfate. Distilled off, ^^ ::: purified by dialysis (hexane), and then recrystallized by ethanol :, and

Pay 7 · 1 g of purified product. C r 9 0 N 2 0 0. 5 I can also reach the following compounds. 2 (3, 4-difluoro) phenyl-6- (trans4-ethyl) cyclohexylnaphthalene 2-(3, 4-difluoro) phenyl-6- (trans4-butyl) cyclohexylnaphthalene 2 (3, 4-difluoro) phenyl-6- (trans 4-pentyl) cyclohexyl ^

Page 65 528794 V. Description of the invention (63) 2- (3, 4, 5-trifluoro) phenyl- 6- (trans 4-ethyl) cyclohexyl naphthalene 2 (3, 4, 5-dirat) benzene -Trans 4-propyl) cyclohexylnaphthalene 2- (3,4,5-trifluoro) phenyl-6- (trans 4-butyl) cyclohexylnaphthalene 2- (3,4,5-trifluoro) Phenyl-6- (trans4-pentyl) cyclohexylnaphthalene [Example 2] 2- (3, 4, 5-trifluoro) phenyl-6- [2- (trans4-propyl) cyclohexyl] Synthesis of Ethylnaphthalene (2-a) Synthesis of 6- (3,4,5-trifluorophenyl) naphthyl-2-yl difluorinite xanthate 20ml of dichloromethane and 34 of trifluoromethanesulfonic anhydride. Og was added with 25.0 g of 6- (3,4,5-tristriphenyl) -2-hydroxynaphthalene and allowed to cool to 5. 〇. 48 ml of a solution of 2.0 g of dichloromethane was added dropwise to this at a temperature not exceeding 20 ° C. After the dropwise addition was completed, the temperature was returned to room temperature under stirring, and 2000 m 1 of water was added. The organic ^ was washed with water and saturated brine, and dried with anhydrous sodium sulfate =. The solvent was purified by silica gel chromatography (the solvent was dichloromethane) to obtain trifluoromethanesulfonated 6- (3,4,5-trifluorophenyl) naphthalene-2-yl 37.3 g. Synthesis of (2-b) 2- (trans4-propcyclohexyl) ethynyl-6- (3,4,5-trifluorophenyl) naphthalene 'r ΪΪ 1methyl ^ 6- (3,4m phenyl ) Naphthalene + group 25.0 g and 1-dihexane were dissolved in 125 ml of N, N-dimethylformamide and triethylamine at 5 (TC temperature) 7 palladium (0) 0.7 § and Copper iodide ("" g, # stir 3 small 4. Allow to cool to room temperature, add to this

1 50 m 1 and 9 laughs by Jia Xiao] Piao, J. Dian, dehydrated saturated sodium chloride with anhydrous sodium sulfate and crystallized to obtain 2- (reverse 4 solvent. Ethanol is used to form a base) naphthalene 17.6 g. Hexyl) ethynyl + (3,4,5-trifluorobenzene

Page 66 Gas) Benthyl-6- [2- (trans4-propyl) cyclohexyl] ethyl 528794 V. Description of the invention (64) (2-c) 2- (3,4,5 ~ Synthesis of naphthalene Trans 4-propcyclohexyl) ethynyl_6_ (3,4,5_trifluorophenyl) naphthalene 17, k dissolved in tetrahydrofuran 400ml 'to this was added 5 g of 5% palladium carbon, 5 kg / cm2 hydrogen & Stir for 6 hours. The catalyst was filtered off, the solvent was distilled off, purified by silica gel chromatography (hexane), and then recrystallized from ethanol to obtain a purified product.

1 1 · 5g. Cr 62 N 134 I can also obtain the following compounds. 2 mono (3,4,5—: gas) phenyl-6 — [2-(trans 4 -ethyl) cyclohexyl] ethylnaphthalene 2 mono (3,4,5— ^ phenyl + [2- (trans 4-Butyl) cyclohexyl] ethylnaphthalene 2-a ^ 3,4,5 digas) phenyl-6- [2- (trans4-pentyl) cyclohexyl] ethylnaphthalene 2-a (3,4, —benzyl -6— [2- (trans4-ethyl) cyclohexyl] ethylnaphthalene 2- (3, 4, -difluoro) phenyl-6— [2 — (trans 4-propyl)

Cr 110 N 166 I 2- (3, 4, -difluoro) phenyl-6- [2 — (trans 4-butyl) cyclohexyl] ethylnaphthalene 2- (3,4, -difluoro) phenyl— 6- [2- — (trans 4-pentyl) cyclohexyl] ethylnaphthalene [Example 3] Synthesis of 2- (3, 4-difluoro) phenyl_6 — (trans 4-vinyl) cyclohexylnaphthalene In Example (1-a), in addition to the use of cyclohexane-4,4, monodione monoethene, acetal π (including the old name "ketal", the same below) instead of 4-propane All of the hexanone were subjected to the Grignard reaction. (Reaction product) After dehydration with potassium hydrogen sulfate, add ethyl ^ a drunk to the grain solution. *-While removing azeotropic water from the system, Heat to reflux. Cool to room temperature, wash sequentially with water, saturated aqueous sodium bicarbonate solution, and saturated brine, and dehydrate with anhydrous sodium sulfate.

Page 67

528794

After drying, the solvent was distilled off to obtain 4_ (6_methoxynaphthalene_2_yl) _3_cyclohexylacetal. This was dissolved in toluene, and contact reduction with olefin was performed in the same manner as in (b), and 'formic acid' was added, followed by heating and mixing. After cooling, water was added, and the toluene layer separated was washed and the solvent was removed. The obtained crude crystals were recrystallized from ethanol to obtain crystals of 4- (6-methoxynaphthalen-2-yl) cyclohexane. This was dissolved in a mixed solvent of toluene and THF and cooled. To this was added a salty hydrazone reagent made of bromoxytriphenyltriphenylscale and potassium tert-butoxide. After returning to room temperature, water and hexane 'were added to remove insoluble matter from the hexane layer, and then the mixture was washed with water / methanol and cereals. After the solvent was distilled off, the solvent was dissolved, dilute hydrochloric acid was added thereto, and the mixture was heated under reflux for 1 hour. After cooling, water was added and extracted with ethyl acetate. After the solvent was distilled off, it was dissolved in ethanol, and a 20% hydrogenated aqueous solution was added thereto, followed by stirring at room temperature. To this was added water, extracted with toluene, washed, dehydrated and dried, and then the solvent was distilled off to obtain crystals of trans 4- (6-methoxybenzene ~ 2 ~ yl) cyclohexylcarbaldehyde. It was dissolved in THF, and to this was added a carbamidine reagent made of phosphonium iodide diphenyl scale and potassium third butoxide. After returning to room temperature, water and hexane were added, and the insoluble matter was removed from the hexane layer by filtration, followed by washing with a water / methanol mixed solvent. After dehydration and drying, the solvent was distilled off, and the residue was purified by silica gel chromatography (曱 笨) to obtain crystals of 2- (transvinylcyclohexyl) -6 ~ methoxynaphthalene. Thereby, the same implementation as (1-c), (1-d), and (ie) was performed to obtain 2- (3,4 ~ monofluoro) benzyl-6- (trans-4-ethenyl) in Sakizaki. ) Cyclohexane. The following compounds can also be obtained. 2- (3,4-difluoro) phenyl-6- [trans 4- (3-butenyl) cyclohexyl] naphthalene 2- (3, 4, 5-trifluoro) phenyl (trans 4-vinyl) Cyclohexyl 2-(3,4,5-trifluoro) phenyl-6 — [trans 4- (3-butenyl) cyclohexyl;] naphthalene

528794 V. Description of the invention (66) Fluoro-2-(3, [Example 4] 1 ^. $, 1 / a, ~ Gaphenyl) -6-propionate, (4-a) 6 -Synthesis of propyl-2-methoxypyrene Synthesis of π-naphthalene In a nitrogen atmosphere, a hydrazone (tribenzamine) made of 6l: propane 125g and magnesium 27§ was added dropwise to a reagent L & The second hospital] nickel (⑴2.5 Kwong Kwang Kwong 0; g and dichloride [1,2-bis, a mixture of liquid. Followed by stirring for 1 day ± = tetra = furan (THF) 200ml Hydrochloric acid 'is used to separate the organic layer, and then it is added with methyl yttrium. In water,', add dilute water, saturated sodium bicarbonate aqueous solution 2 / Bi 4 \ Bi mouth and organic layer, and then dehydrate the dry food by using anhydrous sodium sulfate / 硫酸: 172g of _2-methoxynaphthalene was washed twice. Distillation of the solvent and the synthesis of 6-propyl (4-b) 6-propyl-2 naphthol βδη will be "one of 6-propyl-1 2-" Methenyl naphthalene was added with 680 ml of human acetic acid and 680 ml of 48% hydrobromic acid in the entire amount (172 g) and heated and refluxed to 8 hrs to room temperature. To this was added 3 μm of water, and the deposited crystals were washed with water. The resulting crystals were washed. Dissolved in 10,000 ml of ethyl acetate, water: aqueous solution of sodium bisulfite The salt solution was washed sequentially. After dehydration and drying with sodium hydrate, the solvent was distilled off to obtain 152 g of crude crystals of propyl-2-naphthol. (4-c) 1-fluoro-6-propyl- Synthesis of 2-naphthol to ub) 2 to 6-propyl-2-methoxynaphthyl 20 g and 1.8 g of sodium trimethoate 1.8 g of a carbamidine 80ml solution added bistetrafluoroborate N, N, _Difluoro-2 2, -dioxine II 23.k, and stir for 8 hours. Pour this into water, add dilute hydrochloric acid " knock off the organic layer, and extract the aqueous layer from toluene. Combine the organics The layers were washed sequentially with water and saturated brine, and then dried by anhydrous sodium sulfate.

P.69 528794 V. Description of the invention (67) Cantonese 1) ,, and tun ', and serve Bu_6_propyl ~ 2, i7 ig. (Synthesis of sulfonated 6-propylnaphthyl-6-propylnaphthyl-2-sulfonate from Putian to c. The total amount of fluoro-6-propyl-2-naphthol (17 i) and three = 1 Anhydride 25.lg is dissolved in fine ml of dichloromethane, butt-= 1 hour after incubation, 'dilute hydrochloric acid is added, the organic layer is separated, and the aqueous layer is taken out. The organic layers are combined, and saturated with acetic acid. Shui Shun-After human beings were washed, they were dehydrated and dried by using anhydrous sodium sulphate ^ 七 』乂 #『 乂 乂 木, Germany to remove the solvent, the obtained: one ^ Shixi gel chromatography (hexane) purification, * get three Methoxanthin was acidified with 24.2 g of 1-fluoro6-propanthin-2-yl. (4-e) l-Fluoro-2- (3, 4-difluorophenyl) -6-propylnaphthalene was synthesized by (4- d) 20 g of trifluoromethanesulfonated buflo-6-propenaphthyl-2-yl and dimo (triphenylphosphine) nickel (II) were dissolved in 80 ml of THF, and this was added dropwise under a nitrogen atmosphere 3 '4-Grenia reagent made from 2 5. 8 and 3. 2 g. After stirring for 1 hour, dilute hydrochloric acid was added, the organic layer was separated, and the aqueous layer was extracted with toluene. Combined The organic layer was washed successively with water, a saturated aqueous sodium hydrogen carbonate solution, and a saturated saline solution, and then dried over anhydrous sodium sulfate. After distilling off the solvent media 'of the thus obtained crystals were purified by silica gel chromatography (hexane), to be evaporated

6'g of 1-fluoro-2- (3,4-difluorophenyl) -6-propene naphthalene was obtained. Cr-16 N 13 I can also give the following compound 1-fluoro-2- (3, 4-difluorobenzyl) -6-ethylnaphthalene 1 monofluoro-2- (3,4-difluorophenyl) -6 -Butadiene 1-fluoro ~ 2- (3,4-difluorophenyl) -6-pentaphthalene

Page 70 528794 V. Description of the invention (68) 1-fluoro-2- (3,4-difluorophenyl) -6-hexylnaphthalene 1-fluoro-2- (3,4-difluorophenyl) -6 -Heptaphthalene 1-fluoro-2- (3,4-difluorophenyl) -6- (3-butane) naphthalene 1-fluoro-2- (3,4,5-trifluoroiphenylethylnaphthalene 1-fluoro-2- (3,4,5-trifluorophenyl) -6-propylnaphthalene 1-fluoro-2- (3,4,5-trifluorophenyl) -6-butylnaphthalene 1-fluoro- 2- (3,4,5-tri-phenylphenyl) -6-pentaphthalene 1-fluoro-2- (3,4,5-trifluorophenyl) -6-hexanaphthalene 1-fluoro-2- (3 , 4,5-trifluorophenyl) -6-heptaphthalene

1-fluoro-2- (3,4,5-trifluorophenyl) -6- (3-butanyl) naphthalene 1-fluoro-2- (4-fluorophenyl) -6-ethylnaphthalene 1-gas -2- (4-ILphenyl) -6-propylnaphthalene 1-benzyl-2- (4-fluorophenyl) -6_butylnaphthalene 1-fluoro-2- (4-ILphenyl) -6-pentaphthalene 1-Lan-2- (4-Gaphenyl) -6-hexylnaphthalene 1-fluoro-2- (4-fluorophenyl) -6-heptaphthalene 1-fluoro-2- (4-IL phenyl)- 6- (3 -Butylene) naphthalene 1-fluoro ^ 2- (3-phenylphenyl) -6-ethylnaphthalene

1-fluoro-2- (3-fluorophenyl) -6-propylnaphthalene 1-fluoro-2_ (3-fluorophenyl) -6-butylnaphthalene 1-IL-2- (3-fluorophenyl) -6 -Pentaphthalene 1-fluoro ^ 2- (3-Itphenyl) -6-hexylnaphthalene 1-fluoro-2- (3-fluorophenyl) -6-heptaphthalene 1-fluoro-2- (3-fluorobenzene ) -6- (3 -butenyl) naphthalene

Page 71 528794 V. Description of the invention (69) 1-fluoro-2- (3,5-difluorophenyl) -6-ethylnaphthalene 1-IL-2- (3,5-difluorophenyl) -6 -Propylnaphthalene 1-fluoro-2- (3,5-difluorophenyl) -6-butylnaphthalene 1-fluoro-2- (3,5-difluorophenyl) -6-pentaphthalene 1-It-2 -(3,5-difluorophenyl) -6-hexylnaphthalene 1-fluoro-2- (3,5-difluorophenyl) -6-heptaphthalene 1-benz-2- (3,5-digas Phenyl) -6- (3-butenyl) naphthalene 1-fluoro-2 ~~ phenyl-6_ethynyl 1-gas-2 -phenyl-6-propylnaphthalene

1- It-2 -Phenyl-6-Butylnaphthalene 1-Benzene-2 -Phenyl-6-pentancaine 1-Fluoro-2-phenyl-6-hexanine 1-IL-2 -Phenyl-6- Heptaphthalene 1-Dun-2 -phenyl-6- (3-butenyl) Cai 1-fluoro-2- (4-chlorophenyl) -6-ethylnaphthalene 1-fluoro-2- (4-chlorobenzene ) -6-propylnaphthalene 1-fluoro-2- (4-chlorophenyl) -6-butylnaphthalene 1-fluoro-2- (4-chlorophenyl) -6-pentaphthalene

1-fluoro-2- (4-chlorophenyl) -6-hexylnaphthalene 1-IL-2- (4-chlorophenyl) -6-heptaphthalene 1-fluoro-2- (4-chlorophenyl)- 6- (3 -Butyl) naphthalene 1--fluoro-4-aerophenyl) -6-ethylnaphthalene 1_ IL-2- (3-fluoro-4-chlorophenyl) -6-propylnaphthalene 1-gas -2- (3-Fluoro-4-chlorophenyl) -6-butylene

Page 72 528794 V. Description of the invention (71) 1-Ail-2- (3-IL-4 -trifluoromethoxyphenyl) -6- (3-butenyl) naphthalene 1-fluoro-2- (3 , 5-Digas-4-trispanoxophenyl) -6-ethylnaphthalene1-fluoro-2- (3,5-difluoro-4-trispanoxophenyl) -6-propylnaphthalene1- Fluoro-2- (3,5-difluoro-4 -trifluorofluorenyloxyphenyl) -6-Butylnaphthalene 1-fluoro-2- (3,5-difluoro-4-trifluorofluorenyloxyphenyl)- 6-pentaphthalene 1-fluoro-2- (3,5-difluoro-4-trifluoromethoxyphenyl) -6-hexanaphthalene 1-fluoro-2-(3,5-difluoro-4-trifluoro Methoxyphenyl) -6-heptaphthalene 1-fluoro-2-(3,5 -divinyl-4-trifluoromethoxyphenyl 6- (3-butane) naphthalene 1-fluoro-2-(4 -Digas methoxyphenyl) -6-ethylnaphthalene

1-Gas 2- 2- (4-Difluorofluorenoxyphenyl) -6-propylnaphthalene 1-fluoro-2- (4-difluorenyloxyphenyl) -6-butylene 1-fluoro-2-(4 -Digas methoxyphenyl) -6-pentaphthalene 1-gas-2- (4-diItmethoxyphenyl) -6-hexylnaphthalene 1- 1-2- (4-difluorofluorenyloxyphenyl) -6-Heptaphthalene 1-fluoro-2- (4-difluoromethoxyphenyl) -6- (3-butenyl) naphthalene 1-fluoro-2-(3-fluoro-4 -di-It-methoxybenzene ) -6-ethylnaphthalene 1-gas-2- (3-fluoro-4 -difluoromethoxyphenyl) -6-propylnaphthalene 1-fluoro-2- (3-gas-difluoromethoxyphenyl) -6-Butadiene

1-fluoro-2- (3-fluoro-4 -dioxanyloxyphenyl) -6-pentaphthalene 1-Fluoro-2- (3-Ga-4-DiItmethoxyphenyl) -6-heptaphthalene 1-benz-2-((3-Fluoro-4-difluoroi-methoxyphenyl) -6- ( 3-Butyridyl) naphthalene 1-fluoro-2-(3,5-difluoro-4-difluorofluorenyloxyphenyl) -6-ethylnaphthalene 1-fluoro ^ 2- (3,5-difluoro-4 -Difluoro i phenyloxyphenyl) -6-propylnaphthalene

Page 74 528794 V. Description of the invention (73) 1-fluoro-2- (3, 5-difluoro-4-trifluorofluorenylphenyl) -6-heptaphthalene 1-fluoro-2- (3,5 -di Fluoro-4-trifluorofluorenylphenyl 6- (3-butenyl) naphthalene 1-fluoro-2- (4-methoxyphenyl) -6-ethylnaphthalene 1-fluoro-2- (4-fluorenoxybenzene Yl) -6-propylnaphthalene 1-fluoro-2- (4-fluorenyloxyphenyl 6-butylene naphthalene 1-mer-2- (4-fluorenyloxyphenyl) -6-pentaphthalene 1-fluoro-2- ( 4-Methoxyphenyl) -6-hexylnaphthalene 1-fluoro-2- (4-methoxyphenyl) -6-heptaphthalene 1-fluoro-2- (4-methoxyphenyl) -6- (3 -Butenyl) naphthalene

1-Hex-2- (3-Ga-4-methoxyphenyl) -6-ethylnaphthalene 1-fluoro-2- (3-benzyl-4-methoxyphenyl) -6-propylnaphthalene 1-fluoro- 2- (3-It-methoxyphenyl) -6-butylene 1-fluoro-2-(3-gas-4-methoxyphenyl) -6-pentaphthalene 1-gas-2-(3-fluoro -4-methoxyphenyl) -6-hexylnaphthalene 1-fluoro-2- (3- 1-4-methoxyphenyl) -6-heptaphthalene 1-fluoro-2- (3-dun-4-methyl Oxyphenyl) -6- (3 -butane) Cai 1-mer-2- (3,5-difluoro-4-methoxyphenyl) -6-ethylnaphthalene 1-fluoro-2- (3, 5-difluoro-4-methoxyphenyl) -6-propylnaphthalene

1-fluoro-2-(3,5-difluoro-4-fluorenyloxyphenyl) 6-butylnaphthalene 1-fluoro-2- (3,5-difluoro-4-fluorenyloxyphenyl) -6-pentaphthalene 1-Ga-2- (3,5-difluoro-4-fluorenylphenyl) -6-hexylnaphthalene 1-fluoro-2- (3,5-difluoro-fluorenyloxyphenyl) -6-heptaphthalene 1-fluoro-2- (3,5-digas-4-methoxyphenyl) -6- (3-butanyl) naphthalene 1-fluoro-2- (4-dilute propoxyphenyl) -6- Ethylnaphthalene

Page 76 528794 V. Description of the invention (74) 1-Dun-2- (4-dilute propoxyphenyl) -6-propenaphthalene 1-gas-2- (4-dilute propoxyphenyl) -6-butane Naphthalene 1-fluoro-2- (4-allyloxyphenyl) -6-pentaphthalene 1-gas-2- (4-dilute propoxyphenyl) -6-hexylnaphthalene 1-oxy-2- (4 ~ · Dilute propoxyphenyl-heptaphthalene 1-fluoro-2- (4-allyloxyphenyl) -6- (3-butenyl) naphthalene 1-benz-2- (4-tolyl) -6- Ethylnaphthalene 1-fluoro-2- (4-fluorenyl) -6-propylnaphthalene 1-fluoro-2-(4-tolyl 6-butylnaphthalene

1-fluoro-2- (4-tolyl) -6-pentaphthalene 1-fluoro-2- (4-tolyl) -6-hexylnaphthalene 1-fluoro-2-(4-tolyl) -6-heptane Naphthalene 1-fluoro-2- (4-fluorenyl) -6- (3-butenyl) naphthalene 1-fluoro-butenyl) phenyl] -6-ethylnaphthalene 1-fluoro-2- [4- (3 -Butenyl) phenyl] -6-propylnaphthalene 1-gas-2- [4- (3 -butenyl) phenyl] -6 -butylnaphthalene 1-fluoro-2- [4- (3 -Butenyl) phenyl] -6-pentaphthalene 1-fluoro-2- [4- (3 -butenyl) phenyl] -6-hexylnaphthalene

1-fluoro-2- [4- (3 -butenyl) phenyl] -6-heptaphthalene 1-dun-2- [4- (3 -butanyl) phenyl] -6- (3-butane Diluted) naphthalene 1-fluoro-2- [4- (3,4-difluorophenyl) phenyl) -6-ethylnaphthalene 1-fluoro-2- [4- (3,4-difluorophenyl) Phenyl) -6-propylnaphthalene 1-gas-2- [4- (3,4-difluorophenyl) phenyl) -6-butylnaphthalene 1-fluoro_2- [4- (3,4-di IIphenyl) phenyl) -6-pentaphthalene

Page 77 528794 V. Description of the invention (75) 1-fluoro-2- [4- (3,4-diphenylphenyl) phenyl) -6-hexylnaphthalene 1-fluoro-2- [4- (3, 4-difluorophenyl) phenyl) -6-heptaphthalene 1-gas-2- [4- (3,4-diphenyl) phenyl) -6- (3-butanyl) naphthalene 1-fluoro -2- [4- (3,4,5-trifluorophenyl) phenyl) -6-ethylnaphthalene1-fluoro-2- [4_ (3,4,5-trifluorophenyl) phenyl) ~ ~ 6-Proline naphthalene 1-benz-2- [4- (3,4,5-trifluorophenyl) phenyl) -6-Dingcai 1-IL-2- [4- (3,4,5- Trifluorophenyl) phenyl) -6-pentaphthalenefluoro-2- [4- (3, 4, 5-trifluorophenyl) phenyl) -6-hexylnaphthalene 1-fluoro-2- [4- (3,4,5-trifluorophenyl) phenyl) -6-heptaphthalene 1-fluoro-2- [4- (3, 4, 5-trifluorophenyl) phenyl) -6- (3- Butenyl) naphthalene 1-IL-2- (4- (4-fluorophenyl) phenyl) -6-ethylnaphthalene 1-fluoro-2- (4- (4-phenylphenyl) phenyl) -6 -Propylnaphthalene 1-benzyl-2- (4- (4-phenylphenyl) phenyl) -6-butylnaphthalene 1-fluoro-2- (4- (4-fluorophenyl) phenyl) -6-pentyl Naphthalene 1-fluoro-2- (4- (4-fluorophenyl) phenyl) -6-hexylnaphthalene 1-fluoro2- (4- (4-gasphenyl) phenyl) -6-heptaphthalene 1- Fluoro-2- (4- (4-fluorophenyl) phenyl) -6- (3-butenyl) naphthalene 1- 1 ^ -2- (4- (3-phenylphenyl) benzene ) -6-Ethylnaphthalene 1-fluoro ^ 2- (4- (3-Gaphenyl) phenyl) -6-propylnaphthalene 1-Ga-2- (4- (3-Itphenyl) phenyl)- 6-Butylnaphthalene 1-dun-2- (4- (3--phenylphenyl) phenyl) -6-pentaphthalene 1-di-2- (4- (3-fluorophenyl) phenyl) -6- Hexaphthalene 1-fluoro 2- (4- (3-fluorophenyl) phenyl) -6-heptaphthalene 1-fluoro-2- (4- (3-fluorophenyl) phenyl) -6- (3- Butenyl) naphthalene

Page 78 528794 V. Description of the invention (76) 1-fluoro-2- (4- (3,5-difluorophenyl) phenyl) -6-ethylnaphthalene 1-fluoro-2- (4- (3, 5-difluorophenyl) phenyl) -6-propylnaphthalene 1-gas-2- (4- (3,5-difluorophenyl) phenyl) -6-butylnaphthalene 1-fluoro-2- (4 -(3, 5-difluorophenyl) phenyl) -6-pentaphthalene 1-fluoro ^ 2- (4- (3, 5-difluorophenyl) phenyl) -6-hexylnaphthalene 1-fluoro- 2- (4- (3, 5-difluorophenyl) phenyl) -6-heptaphthalene 1-fluoro-2_ (4- (3,5-difluorophenyl) phenyl) -6- (3- Butenyl) naphthalene 1-fluoro-2- (4- (4-chlorophenyl) phenyl) -6-ethylnaphthalene 1-fluoro-2- (4- (4-chlorophenyl) phenyl) -6 -Pronaphthalene

1-fluoro-2- (4- (4-chlorophenyl) phenyl) -6-butylnaphthalene1-fluoro-2- (4- (4-chlorophenyl) phenyl) -6-pentaphthalene1- Fluoro-2_ (4- (4-chlorophenyl) phenyl) -6-hexylnaphthalene 1-benz-2- (4- (4-chlorophenyl) phenyl) -6-heptaphthalene 1-fluoro-2 -(4- (4-chlorophenyl) phenyl) -6- (3-butenyl) naphthalene 1-fluoro-2_ (4- (3-chlorophenyl) phenyl) -6-ethylnaphthalene 1- Fluoro-2- (4- (3-chlorophenyl) phenyl) -6-propanthine 1-fluoro-2- (4- (3-chlorophenyl) phenyl) -6-butanthine 1-fluoro- 2- (4- (3-chlorophenyl) phenyl) -6-pentaphthalene

1-fluoro-2- (4- (3-chlorophenyl) phenyl) -6-hexylnaphthalene 1-fluoro-2- (4- (3-chlorophenyl) phenyl) -6-heptaphthalene 1- Mole-2- (4- (3-fluoro-4-chlorophenyl) phenyl) -6- (3-butanyl) naphthalene 1-fluoro-2- (4- (3,5-difluoro-4 -Chlorophenyl) phenyl) -6-ethylnaphthalene1-fluoro ^ 2- (4- (3,5-difluoro-4-chlorophenyl) phenyl) -6-propylnaphthalene 1-fluoro-2- (4- (3,5-difluoro-4-chlorophenyl) phenyl) -6-butylene

Page 79 528794 V. Description of the invention (77) 1-Ga-2- (4- (3,5-difluoro-4-chlorophenyl) phenyl) -6-pentaphthalene 1-It-2- (4 -(3,5-difluoro-4-chlorophenyl) phenyl) -6-hexylnaphthalene1-fluoro-2- (4- (3,5-difluoro-4-chlorophenyl) phenyl)- 6-heptaphthalene 1-gas-2- (4- (3,5-di4-chlorophenyl) phenyl) -6- (3-butenyl) naphthalene

1-fluoro-2- (4- (4-tri-IL-methoxyphenyl) phenyl) -6-ethylnaphthalene1-fluoro-2- (4- (4-tri-ILmethoxyphenyl) phenyl)- 6-propylnaphthalene 1-fluoro 2- (4- (4-trifluorofluorenyloxyphenyl) phenyl) -6-tetranaphthalene 1-gas-2- (4- (4-trifluoromethoxyphenyl) benzene Yl) -6-pentaphthalene 1-gas-2- (4- (4-trifluoromethoxyphenyl) phenyl) -6-hexylnaphthalene 1-benz-2-(4- (4-trifluoromethoxy Phenyl) phenyl) -6-heptaphthalene 1-fluoro-2- (4- (4-trifluoromethoxyphenyl) phenyl) -6- (3-butenyl) naphthalene 1-fluoro-2- ( 4- (3-Ga-4-trifluorofluorenyloxyphenyl) phenyl) -6-ethylnaphthalene1-fluoro-2- (4- (3-fluoro-4-trifluoromethoxyphenyl) phenyl) -6 -Proline naphthalene 1-fluoro-2-(4--(3-Ga-4 -trifluoromethoxyphenyl) phenyl)-6 -Butylnaphthalene 1-fluoro-2- (4- (3-fluoro- 4-trifluoromethoxyphenyl) phenyl) -6-pentaphthalene 1-gas-2- (4- (3-IL-4 -tri-IL-oxophenyl) phenyl) -6-hexylnaphthalene 1- It -2- (4- (3-Fluoro-4-tridenmethoxyphenyl) phenyl) -6-heptaphthalene 1-benz-2- (4- (3-fluoro-4-trifluorofluorenyloxybenzene) Phenyl) -6- (3-butyridinyl) naphthalene 1-fluoro-2- (4- (3,5-difluoro-4 -trifluorojmethoxyphenyl) phenyl) -6-ethyl Naphthalene 1-Di-2- (4- (3,5-difluoro-4-tri-IL) Phenyl) phenyl) -6-propylnaphthalene 1-fluoro-2- (4- (3,5-difluoro-4 -trifluoromethoxyphenyl) phenyl) -6-butylnaphthalene 1-fluoro-2 -(4- (3,5-difluoro-4-trifluoromethoxyphenyl) phenyl) -6-pentaphthalene

Page 80 528794 V. Description of the invention (78) 1-fluoro-2- (4- (3,5-diH-4 -tri-Itmethoxyphenyl) phenyl) -6-hexylnaphthalene 1-IL-2 -(4- (3,5 -digas-4 -trifluoroioxophenyl) phenyl) -6 -heptaphthalene 1 -fluoro-2- (4- (3,5 -digas-4 -tri Fluoroxophenyl) phenyl) -6- (3-butenyl) naphthalene

1-Dun-2- (4- (4-trifluorofluorenyloxyphenyl) phenyl) -6-ethylnaphthalene 1-fluoro-2- (4- (4-trifluorofluorenyloxyphenyl) phenyl 6- Propinaphthalene 1-fluoro-2- (4- (4-trifluorofluorenyloxyphenyl) phenyl) -6-butylnaphthalene 1-fluoro ^ 2- (4- (4-triILmethoxyphenyl) phenyl ) -6-pentaphthalene 1-fluoro-2- (4- (4-trifluoromethoxyphenyl) phenyl) -6-hexylnaphthalene 1-fluoro-2-(4- (4-trifluorofluorenyloxybenzene) Phenyl) -6-heptaphthalene 1-fluoro-2-(4- (4-diitmethoxyphenyl) phenyl) -6- (3-butenyl) naphthalene 1-fluoro-2- ( 4- (3-fluoro-4 -difluoromethoxyphenyl) phenyl) -6-ethylnaphthalene 1--2--2- (4- (3-fluoro-4-difluoroi-methoxyphenyl) phenyl ) -6-propylnaphthalene 1-benz-2- (4- (3-gas-4-difluoromethoxyphenyl) phenyl) -6-butylnaphthalene 1-dun-2- (4- (3-fluoro -4 -Digas methoxyphenyl) phenyl) -6-pentaphthalene 1-fluoro-2- (4- (3-fluoro-4 -difluoromethoxyphenyl) phenyl) -6-hexylnaphthalene 1 -Ga-2-(4- (3-Ga-4 -difluorofluorenyloxyphenyl) phenyl) -6-heptaphthalene 1-fluoro-2- (4- (3-fluoro-4-difluoromethoxy) Phenyl) phenyl) -6- (3-butylfluorenyl) naphthalene 1-1-2- (4- (3,5-di-4 -difluoroamidooxyphenyl) phenyl) -6-ethylnaphthalene 1-Ga-2-(4- (3,5-difluoro-4-difluoromethoxybenzene ) Phenyl) -6-propylnaphthalene 1-fluoro1-2- (4- (3,5-difluoro-4-dimethoxymethoxyphenyl) phenyl) -6-butylnaphthalene 1-fluoro-2- (4- (3, 5-difluoro-4-difluorofluorenyloxyphenyl) phenyl) -6-pentaphthalene 1-fluoro-2- (4- (3,5-digas-4-digasamidine) Oxyphenyl) phenyl) -6-hexyl naphthalene

Page 81 528794 V. Description of the invention (79): 1-fluoro-2- (4-(3, 5-difluoro-4-di1-fluoro-2- (4- (3,5 -difluoro-4) -Dienyl) naphthalene 1-benz-2- (4- (4-trifluorofluorenyl) 1-gas-2- (4- (4-trifluorotolyl) 1-IL-2- (4- (4-trifluorotolyl) 1-It-2- (4- (4-trifluorotolyl) 1-Fluoro 2- (4- (4-trifluorotolyl) 1-gas-2-(4 -(4-trifluorotolyl) 1-fluoro-2- (4- (4-tri11tolyl) 1-IL-2- (4- (3-fluoro-4 -trifluoromethyl 1-fluoro-2 -(4- (3-It-4 -tri-IL a 1-IL-2- (4- (3-fluoro-4 -trifluorom-l-fluoro-2- (4- (3-It-4 -tri IL 曱 1-fluoro-2- (4- (3-fluoro-4-tri IL A 1-fluoro-2- (4--(3- 3 -Ga-4 -Trispinylnaphthalene 1-fluoro-2- (4- (3, 5-difluoro-4-tri 1-I -2- (4- (3,5 -difluoro-4-tri 1-it-2-(4- (3,5-diit-4 -tri-1-fluoro-2- (4- (3, 5-difluoro-4-1-IL -2- (4- (3 , 5-difluoro-4-1-fluoro-2- (4- (3, 5-difluoro-4-fluoromethoxyphenyl) phenyl) -6-heptaphthylfluoroimethoxyphenyl) phenyl ) -6- (3-Butylphenyl) -6-ethylnaphthylphenyl) -6-propylnaphthylphenyl) -6-butylnaphthylphenyl) -6-pentaphthylphenyl) -6-hexylnaphthylphenyl )- 6-heptaphthylphenyl) -6- (3-butanyl) naphthylphenyl) phenyl) -6-ethylnaphthylphenyl) phenyl) -6-propylnaphthylphenyl) phenyl) -6-butyl Naphthylphenyl) phenyl) -6-pentaphthylnaphthyl) phenyl) -6-hexylnaphthylphenyl) phenyl) -6-heptaphthylphenyl) phenyl) -6- (3-butenyl) Fluorofluorenyl) phenyl) -6-ethylnaphthylfluorinylphenyl) phenyl) -6-propylnaphthylfluorotolyl) phenyl) -6-butylnaphthylfluorotolyl) phenyl) -6-pentaphthalene Fluorofluorphenyl) phenyl) -6-hexylnaphthalene

Page 82 528794 V. Description of the invention (80) 1-Ga-2- (4- (3,5-difluoro-4 -trifluorofluorenylphenyl) phenyl) -6- (3 -butane) naphthalene

1-mer-2- (4- (4-methoxyphenyl) phenyl) -6-ethylnaphthalene 1-fluoro-2-(4- (4-methoxyphenyl) phenyl 6-propylnaphthalene 1- Fluoro-2- (4- (4-methoxyphenyl) phenyl) -6-butynaphthyl-2- (4- (4-methoxyphenyl) phenyl) -6-pentaphthalene 1-fluoro 2- (4- (4-methoxyphenyl) phenyl) -6-hexylnaphthalene 1-fluoro-2- (4- (4-methoxyphenyl) phenyl) -6-heptaphthalene 1-fluoro -2- (4- (4-methoxyphenyl) phenyl) -6- (3-butane) naphthalene 1-benz-2- (4- (3-fluoro-4-methoxyphenyl) benzene ) -Ethylnaphthalene 1- Dun-2- (4- (3-fluoro-4-methoxyphenyl) phenyl) -6-propylnaphthalene 1-IL-2- (4- (3-fluoro-4- Methoxyphenyl) phenyl) -6-Butylnaphthalene1-benzyl-2- (4- (3-benzyl-4-methoxyphenyl) phenyl) -6-pentaphthalene1-fluoro-2-(4 -(3-Gas-4-methoxyphenyl) phenyl) -6-hexylnaphthalene 1-gas-2- (4- (3-fluoro-4-methoxyphenyl) phenyl) -6-heptaphthalene 1-IL- 2-(4-(3-fluoro-4-methoxyphenyl) phenyl) -6- (3-butenyl) naphthalene 1-town-2- (4- (3,5-difluoro -4-Azophenyl) phenyl) -6-ethylnaphthalene 1-gas-2- (4- (3,5-difluoro-4-methoxyphenyl) phenyl) -6-propylnaphthalene 1- -2-(4- (3,5-difluoro-4-fluorenyloxyphenyl) phenyl) -6-butylnaphthalene 1-gas-2- (4- (3 5-diIL-4-methoxyphenyl) phenyl) -6-pentaphthalene 1-town-2- (4- (3,5-difluoro-4-methoxyphenyl) phenyl) -6- Hexaphthalene 1-It-2- (4- (3,5-difluoro-4-methoxyphenyl) phenyl) -6-heptaphthalene 1-mer-2- (4-(3,5-diIL 4-Azulenoxyphenyl) phenyl) -6- (3-butynyl) naphthalene

Page 83 528794 V. Description of the invention (81) 1-fluoro-2- (4- (4- (allyloxyphenyl) phenyl) -6-ethylnaphthalene 1-fluoro-2- (4- (4--ene Propoxyphenyl) phenyl) -6-propylnaphthyl-2- (4- (4-allyloxyphenyl) phenyl) -6-butylnaphthalene 1-fluoro-2- (4- (4- Allyloxyphenyl) phenyl) -6-pentaphthalene 1-fluoro-2- (4- (4-allyloxyphenyl) phenyl) -6-hexylnaphthalene 1-fluoro-2- (4- ( 4-dilute propoxyphenyl) phenyl) -6-heptaphthalene 1-fluoro-2- (4- (4-dilute propoxyphenyl) phenyl) -6- (3-butane) naphthylfluoro 2- (4- (4-Tolyl) phenyl) -6-ethylnaphthalene 1-benzyl-2- (4- (4-tolyl) phenyl) -6-propylnaphthalene

Buflo-2- (4- (4-tolyl) phenyl) -6-butane-naphthalene 1-fluoro-2- (4- (4-tolyl) phenyl) -6-pentaphthalene 1-fluoro-2 -(4- (4-Tolyl) phenyl) -6-hexylnaphthalene 1-fluoro-2- (4- (4-tolyl) phenyl) -6-heptaphthyl-2- (4- ( 4-Tolyl) phenyl) -6- (3-butenyl) naphthalene 1-fluoro-2- (4- (3-butenephenyl) phenyl) -6-ethylnaphthalene 1-fluoro-2- (4- (3-butyl diphenyl) phenyl) -6-propanephthalene 1- 1-2- (4- (3-butyl diphenyl) phenyl) -6 -butylnaphthalene 1-fluoro-2- (4- (3-Butyrylphenyl) phenyl) -6-pentaphthalene

1-fluoro-2- (4- (3-butanephenyl) phenyl) -6-hexyl 1-fluoro-2- (4- (3-butenephenyl) phenyl) -6-heptaphthalene 1 -Fluoro-2- (4- (3-butenyl) phenyl) -6- (3-butenyl) naphthalene 1-fluoro-2- (3-fluoro-4- (3,4-di Phenyl) phenyl 6-ethylnaphthalene 1-dun-2- (3-IL-4- (3,4-dioxophenyl) phenyl) -6-propylnaphthalene 1-gas-2- (3-fluoro -4- (3,4-diIL phenyl) phenyl) -6-butylene

Page 84 528794 V. Description of the invention (82) 1-fluoro-2- (3- | L-4- (3,4-diphenylphenyl) phenyl) -6-pentaphthalene 1-fluoro-2- ( 3-Dun-4- (3,4-difluorophenyl) phenyl) -6-hexylnaphthalene 1-fluoro-2- (3-fluoro-4- (3,4-difluorophenyl) phenyl) -6-heptaphthalene 1-II-2- (3- 4- (3,4-difluorophenyl) phenyl) -6- (3-butanyl) naphthalene 1-fluoro-2- (3-fluoro -4- (3,4,5-trifluorophenyl) phenyl) -6-ethylnaphthalene 1-fluoro-2- (3-fluoro-4- (3, 4, 5-trifluorophenyl) phenyl ) -6-propylnaphthalene 1-fluoro-2- (3-IL-4- (3,4,5-trilactyl) phenyl) -6-butylnaphthalene 1-benzyl-4- (3,4, 5 -tri-phenyl) phenyl) -6-pentaphthalene

1-fluoro-2- (3-deca-4- (3,4,5-tri-Itphenyl) phenyl) -6-hexylnaphthalene 1-fluoro-2- (3-deca-4- (3,4 , 5-trifluorophenyl) phenyl) -6-heptaphthalene 1-fluoro-2- (3-fluoro-4- (3,4,5-trifluorophenyl) phenyl) -6- (3-butane Diluted) naphthalene 1-fluoro-2- (3-fluoro-4- (4-fluorophenyl) phenyl) -6-ethylnaphthalene 1-benz-2- (3-IL-4- (4-fluorobenzene Phenyl) -6-propylnaphthalene 1-fluoro-2- (3-fluoro-4 (4-fluorophenyl) phenyl) -6-butylnaphthalene 1-IL_2- (3-Ga-4- ( 4-Gasphenyl) phenyl) -6-pentaphthalene 1-fluoro-2- (3-fluoro-4- (4-fluorophenyl) phenyl) -6-hexylnaphthalene

1-fluoro-2- (3-fluoro- 4- (4-Gaphenyl) phenyl) -6-heptaphthalene 1-fluoro-2- (3-gas- 4- (4-phenylphenyl) phenyl ) -6- (3 -butane) naphthalene 1-gas-2- (3-fluoro- 4- (3-fluorophenyl) phenyl) _6-ethylnaphthalene 1-fluoro ^ 2- (3-gas- 4- (3-fluorophenyl) phenyl) -6-propylnaphthalene 1-fluoro-2- (3-fluoro- 4- (3-fluorophenyl) phenyl) -6 -butylnaphthalene 1-fluoro-2 -(3-fluoro-4- (3-Iphenyl) phenyl) -6-pentaphthalene

Page 85 528794 phenyl) phenyl) -6-hexylnaphthylphenyl) phenyl) -6-heptaphthylphenyl) phenyl) -6- (3-butenyl) naphthyldifluorophenyl) phenyl ) -6-Ethylnaphthyldifluorophenyl) phenyl) -6-Propernaphthyldifluorophenyl) phenyl) -6-Butylnaphthyldifluorophenyl) phenyl) -6-pentaphthalenedifluorophenyl) Phenyl) -6-hexylnaphthalenedifluorophenyl) phenyl) -6-heptaphthylenediIIphenyl) phenyl) -6- (3-butenyl) 5. Description of the invention (83) 1-fluoro- 2- (3-1-Gas-2- (3-1-Fluoro-2- (3-1-Fluoro-2- (3-1-Fluoro-2- (3-1-Fluoro-2- (3- 1-Ga-2_ (3-1-Ga-2- (3-1-Fluoro-2-O-fluorene-Fluoro-2- (3-naphthalene 1-Fluoro-2- (3-BuFluoro-2-( 3-1-Fluoro-2- (3-1-Fluoro-2- (3-1-Ga-2- (3-1-Fluoro-2- (3-1-Xiang-2- (3-1-Fluoro -2- (3-1-Fluoro-2- (3-1-Fluoro-2- (3-1-Fluoro-2-O-fluorene-defeated-2- (3-1-Gas-2- (3- Gas-4- (3-fluorofluoro-4- (3-dunIL-4- (3-fluoroIL-4- (3,5-fluoro-4- (3,5-dun-4- (3,5 -Fluoro-4- (3,5-fluoro-4- (3,5-mer-4- (3,5-dun-4- (3,5-gas-4- (4-chlorophenyl)) fluoro- 4- (4-chlorophenyl) mer-4- (4-chlorophenyl) fluoro-4- (4-chlorophenyl) fluoro-4- (4-chlorophenyl) It-4- (4-chlorophenyl) Phenyl) -4- (4-Gaphenyl) fluoro-4- (3-lt-4-chlorofluoro-4- (3-fluoro-4- Chlorine-4- (3-fluoro-4-chlorofluoro-4- (3-fluoro-4-chlorotown-4- (3-gas-4-chlorofluoro-4- (3-fluoro-4-chlorophenyl ) -6-Ethylnaphthyl) -6-naphthylphenyl) -6-Butylnaphthyl) -6-pentaphthylphenyl) -6-hexylnaphthyl) -6-heptaphthylphenyl) -6- (3-butenephenyl) phenyl) -6-ethylphenyl) phenyl) -6-propylphenyl) phenyl) -6-butylphenyl) phenyl) -6-pentylphenyl) phenyl ) -6-hexylphenyl) phenyl) -6-heptyl) naphthalenenaphthalenenaphthalenenaphthalenenaphthalenenaphthalenenaphthalenenaphthalene

Page 86

I 528794 V. Description of the invention (84) 1-fluoro-2- (3-IL-4- (3-fluoro-4-chlorophenyl) phenyl) -6- (3-butenyl) naphthalene 1-fluoro -2- (3-1-Fluoro-2- (3-1-Fluoro-2- (3-1-Fluoro-2-O-fluorene-Fluoro-2-(3-1-Fluoro-2- (3- 1-2- (3-alkenyl) naphthalene 1-air-2- (3-1-fluoro-2- (3-1-fluoro-2-O-fluorene-fluoro-2- (3 -1- Fluoro-2- (3-1-benz-2- (3-1-fluoro-2- (3-yl) naphthalene 1-fluoro-2-0-fluorene-fluoro-2- (3-fluoro-4- ( 3, 5-II-4- (3,5-IL-4 ~ (3, 5 ~ Fluoro-4- (3, 5-IL-4- (3, 5-Fluoro-4- (3,5- -4- (3,5-H-4-chlorophenyl) phenyl) -6-ethylnaphthalenefluoro-4-chlorophenyl) phenyl) -6-propylnaphthalene It-4 -chlorophenyl) phenyl ) -6-Butylnaphthalenefluoro-4-chlorophenyl) phenyl) -6-pentaphthaleneH-4-chlorophenyl) phenyl) -6-hexylnaphthalenefluoro-4-chlorophenyl) phenyl)- 6-heptaphthyl-4-chlorophenyl) phenyl) -6- (3-fluorene-4- (4-trifluoromethoxyphenyl) phenyl) -6-ethylnaphthyl-4- (4 -Tridecylmethoxyphenyl) phenyl) -6-propylnaphthalene 1-4 (4-trifluoro1methoxyphenyl) phenyl) -6 -butylnaphthalenefluoro-4 4- (4-trifluoromethoxy) Phenyl) phenyl) -6-pentaphthylfluoro-4- (4-trifluorofluorenyloxyphenyl) phenyl) -6-hexanaphthyl-1,4-mono (4-trifluorofluorenyloxyphenyl) phenyl )-6-Heptaphthyl-4 -(4-trifluoromethoxyphenyl) phenyl) -6- (3-butane-IL-4-(3--4 -gas-4- (3- 敦 -4-H-4- (3- Fluoro-4-fluoro-4- (3- as-4-fluoro-4- (3-fluoro-4- 1-fluoro-2- (3-1-fluoro-2-(3-1-fluoro-2- (3-1-Ga-2-(3-Ga-4- (3-fluoro-4 -fluoromethoxyphenyl) phenyl) -6-ethinaphthylfluoromethoxyphenyl) phenyl) -6-propyl Naphthylfluoromethoxyphenyl) phenyl) -6-butylnaphthylfluoromethoxyphenyl) phenyl) -6-pentaphthalenefluoromethoxyphenyl) phenyl) -6-hexanaphthylfluoromethoxyphenyl) benzene Base) -6_heptaphthalene

Page 87 528794 V. Description of the invention (85) 1-fluoro-2- (3- | L-4- (3-fluoro-4-trifluoromethoxyphenyl) phenyl) -6- (3-butene Yl) naphthalene 1- Dun-2- (3-fluoro-4- (3,5-digas-4-trifluorofluorenoxyphenyl) phenyl) -6-ethylnaphthalene 1--2--2- (3- IL -4- (3,5 -digas-4 -tri-n-methoxyphenyl) phenyl 6-propylnaphthalene 1-fluoro-2- (3-fluoro-4- (3, 5-difluoro-4- Trifluoromethoxyphenyl) phenyl) -6-butylene 1-It-2- (3-fluoro-4- (3,5-difluoro-4 -trifluoromethoxyphenyl) phenyl) -6 -Pentaphthalene 1-fluoro-2- (3-gas-4-(3,5 -digas-4 -trifluoromethoxyphenyl) phenyl) -6-hexylnaphthalene 1 -tun-2-(3- Fluoro-4- (3,5-difluoro-4-trifluoromethoxyphenyl) phenyl) -6-heptaphthalene1-fluoro-2- (3-fluoro-4- (3, 5-difluoro- 4-trifluoromethoxyphenyl) phenyl) -6- (3-butane) naphthalene; 1-fluoro-2- (3-fluoro-4- (4-difluorofluorenoxyphenyl) phenyl) -6-Ethylnaphthalene 1-fluoro-2-(3-fluoro-4- (4-difluoromethoxyphenyl) phenyl) -6-propylnaphthalene 1-IL-2- (3-fluoro-4- ( 4-difluoromethoxyphenyl) phenyl) -6-butyrnaphthalene1-gas-2-(3-fluoro-4- (4-difluoromethyloxyphenyl) phenyl) -6-pentaphthalene1- Fluoro-2-(3-fluoro-4- (4-difluoroimethoxyphenyl) phenyl 6-hexylnaphthalene 1-gas-2 -(3-fluoro ^ 4- (4-diItmethoxyphenyl) phenyl) -6-heptaphthalene 1-gas-2- (3-fluoro-4- (4-difluoromethoxyphenyl) benzene ) -6_ (3-butenyl) naphthalene

Page 88 528794 V. Description of the invention (86) 1-fluoro-2- (3-fluoro-4- (3-fluoro-4-difluorofluorenyloxyphenyl) phenyl) -6-ethylnaphthalene 1-fluoro- 2- (3-fluoro-4- (3-fluoro-4 -difluorofluorenoxyphenyl) phenyl) -6-propylnaphthalene 1-fluoro-2- (3-fluoro-4- (3- II-4 -Difluorofluorenyloxyphenyl) phenyl 6-butylnaphthalene1- 1-2- (3-debran-4- (3 -lan-4-dioxaphenyloxyphenyl) phenyl) -6-pentaphthalene1 -Fluoro-2-(3-Gas 4- (3-Gas-4 -Digas oxophenyl) phenyl) -6-hexylnaphthalene 1-fluoro-2- (3-fluoro-4- (3- Fluoro-4-difluorofluorenyloxyphenyl) phenyl) -6-heptaphthalene 1-dun-2-(3-fluoro-4- (3- 4 -dimethoxymethoxyphenyl) phenyl) -6- (3-butenyl) naphthalene

1-Ga-2- (3-Dun-4- (3,5-difluoro-4 -difluorofluorenoxyphenyl) phenyl) -6-ethylnaphthalene 1 _ ^-2- (3-fluoro-4- (3,5-difluoro-4 -difluoromethoxyphenyl) phenyl) -6-propylnaphthalene 1-fluoro-2-(3-benzyl-4_ (3,5-digas-4 -difluorofluorene) Oxyphenyl) phenyl) -6-butylnaphthalene 1-fluoro-2- (3-fluoro-4- (3,5 -difluoro-4 -diIt oxophenyl) phenyl) -6-pentaphthalene 1-fluoro-2- (3-fluoro-4- (3, 5-difluoro-4-difluoromethoxyphenyl) phenyl) -6-hexylnaphthalene

1-fluoro-2- (3-fluoro-4- (3,5-difluoro-4 -difluorofluorenoxyphenyl) phenyl) -6-heptaphthalene 1-fluoro-2- (3-fluoro-4 -(3, 5-difluoro-4-difluorofluorenyloxyphenyl) phenyl) -6- (3 -butane) naphthalene 1-fluoro-2- (3-gas-4- (4-trifluoro Stilbene) phenyl) -6-ethylnaphthalene 1-gas-2- (3-fluoro-4- (4-trifluorostilbenephenyl) phenyl) -6-propylnaphthalene

Page 89, 528794 V. Description of the invention (87) 1-Defeat-2- (3-1-IL -2- (3-1-Fluoro-2- (3-1-Fluoro-2- (3-1 ~ | L-2- (3-naphthalene 1-fluoro-2- (3-1-gas-2- (3-1-fluoro-2- (3-1-fluoro-2- (3-1-defeat-2- (3-1- 11-2- (3-1-fluoro-2- (3-alkenyl) naphthalene 1-fluoro-2- (3-naphthalene 1-fluoro-2- (3-naphthalene 1-fluoro-2 -(3-naphthalene 1-fluoro-2- (3-naphthalene 1-fluoro-2-(3-naphthalene gas-4- (3-fluoro-4-fluoro-4- (3- It-4-fluoro-4 -(4-trifluorofluorenyl) phenyl) -6-butylnaphthylfluoro-4- (4-trifluorofluorinyl) phenyl) -6-pentaphthylfluoro-4- (4-trifluorofluorene Phenyl) -6-hexylnaphthylfluorenylphenyl) phenyl) -6-heptaphthylnaphthylphenyl) phenyl) -6- (3 -butenyl) Ga-4- (3-Ga- 4_trifluorotolyl) phenyl) -6-ethylnaphthalene It-4- (3-fluoro-4 -trifluorofluorenylphenyl) phenyl) -6-propylnaphthalenefluoro-4- (3-fluoro-4 -Trifluorotolyl) phenyl) -6-tetranaphthylfluoro-4- (3-anil-4_trifluorotolyl) phenyl) -6 -pentanaphthyl-4- (3-fluoro ^ 4 -tri Fluorotolyl) phenyl) -6-hexylnaphthylfluorotolyl) phenyl) -6-heptaphthylnaphthylfluorotolyl) phenyl) -6- (3- 1fluoro-4- (3,5-difluoro- 4-trifluorofluorenyl) phenyl) -6-ethylIL-4- (3,5-difluoro-4-trifluorofluorinyl) phenyl) -6-propylfluoro- 4- (3,5-difluoro-4-trifluorotolyl) phenyl) -6-butafluoro-4- (3, 5-difluoro-4-trifluorotolyl) phenyl) -6-pentyl Fluoro-4- (3,5-difluoro-4-trifluorotolyl) phenyl) -6_hex

Page 90 528794 V. Description of the invention (88) 1-gas-2- (3-fluoro-4- (3,5-difluoro-4-trifluorotolyl) phenyl) _6-heptaphthalene 1-fluoro- 2- (3- (3-butylfluorenyl) naphthalene 1-IL- 2-(3-1-fluoro-2- (3-1-milk-2- (3-fluoro-4- (4-1-it -2-(3-defeat _ 4-(4 -1-IL-2-(3-IL-4-(4-1- as far as 2- (3-fluoro-4- (4-1-as -2 -(3-fluoro-4- (3,5-difluoro-4-trifluorofluorenylphenyl) phenyl) -6-fluoro-4- (4-fluoro-4- (4-methoxyphenyl) fluorene Oxyphenyl) Methoxyphenyl) Methoxyphenyl) Methoxyphenyl) Methoxyphenyl) 1-Di-2- (3-1-Ga-2- (3-1- 2- (3-1 -Fluoro-2- (3- 1-fluoro-2- (3-1-fluoro-2- (3-1-fluoro-2- (3-fluoro-4_ (3- then-4- (4-methoxy) Phenyl) fluoro-4- (3-fluoro-4-fluorenyloxyfluoro-4- (3-fluoro-4- (3-fluoro-4- (3-gas-4- (3_gas-4-hydrazone) Fluoro-4- (3 -fluoro-4-methoxyfluoro-4-methoxy H_4-methoxyfluoro-4-fluorenylfluoro-4-methoxyphenyl) -6-ethylnaphthylphenyl) _6-propylnaphthalene Phenyl) -6-butylnaphthylphenyl) -6-pentaphthylnaphthyl) -6-hexylnaphthylphenyl) _6-heptaphthylnaphthyl) -6- (3-butenyl) naphthylphenyl) phenyl ) -6-Ethylnaphthylphenyl) phenyl) -6-Pronaphthylphenyl) Phenylnaphthylphenyl) Phenyl) -6-pentaphthylphenyl Phenyl) -6-hex-naphthyl) phenyl) -6-heptan-naphthyl) phenyl) -6- (3 - butoxy dilute

) Naphthyl-4- (3,5-diII-4-fluorenylphenyl) phenyl) -6-ethylnaphthylfluoro-4- (3,5-difluoro-4-methoxyphenyl) benzene Yl) -6-propynapenefluoro-4- (3,5-difluoro-4-fluorenyloxyphenyl) phenyl) -6-butylnaphthalene 1-fluoro-2- (3-fluoro-4- (3, 5-difluoro-4-methoxyphenyl) phenyl) -6-pentaphthalene 1-fluoro-2- (3-fluoro-4- (3, 5-difluoro-4-methoxyphenyl) phenyl ) -6-Hexaphthalene 1-Ga-2- (3-1-Ga-2- Ο-ΐ-It-2-(3-

I

Page 91 528794 V. Description of the invention (89) 1-fluoro-2- (3-1-fluoro-2- (3-butenyl) naphthalene 1-fluoro-2- (3-1-fluoro-2-( 3-1-fluoro-2- (3-1-fluoro-2- (3-1-fluoro-2- (3-1-fluoro-2- (3-1-fluoro-2- (3-naphthalenefluoro- 2- (3-1-fluoro-2- (3-1-fluoro-2- (3-1-fluoro-2- (3-1-fluoro-2- (3-1-gas-2- (3- 1-Dun-2- (3-1-Fluoro-2- (3-1-It-2- (3-1-Fluoro-2-O-fluorene-fluoro-2- (B-fluorene-fluoro-2- (3-1-fluoro-2- (3-fluoro-4- (3,5-diden-4-methoxyphenyl) phenyl) -6-heptaphthonafluoro-4- (3,5-difluoro -4-methoxyphenyl) phenyl) -6- (3-fluoro-4- (4-allyloxyphenyl) fluoro-4- (4-allyloxyphenyl) fluoro-4- (4- Diluted propoxyphenyl) fluoro-4_ (4-allyloxyphenyl) fluoro-4- (4-allyloxyphenyl) fluoro-4- (4-dipropoxyphenyl) fluoro-4- (4 -Allyloxyphenyl) Phenyl) -6-Pernaphthylphenyl) -6-Propernaphthylphenyl) -6-Butylnaphthylphenyl) -6-Pentaphthylphenyl) -6-hexylnaphthylphenyl) -6-heptaphthylphenyl) -6- (3 -butenyl) a 4- (4-tolyl) fluoro-4- (4-tolyl) gas-4- (4-tolyl) fluorine- 4- (4-fluorenyl) It-4- (4-fluorenyl) fluoro-4- (4-fluorenyl) fluoro-4- (4-fluorenyl) fluoro-4- (4- ( 3-butenefluoro-4- (4- (3-butenefluoro-4- (4- (3- Butenefluoro-4- (4- (3-butenefluoro-4- (4- (3-butenefluoro-4- (4- (3-butenephenyl) -6- Ethyl-naphthyl) -6-propylnaphthyl) -6-butylnaphthyl) -6-pentaphthyl) -6-hexylnaphthyl) -6-heptaphthyl) -6- (3 -Butylenes) Naphthylphenyl) phenyl))-6-Ethylnaphthylphenyl) phenyl))-6-Pronaphthylphenyl) phenyl)) _ 6-Butylnaphthylphenyl) phenyl))-6 -Pentaphthylphenyl) phenyl)) _ 6-hexylnaphthylphenyl) phenyl))-6-heptaphthalene

Page 92

528794 V. Description of the invention (90) 1-fluoro-2- (3-fluoro- 4- (4- (3-butyrophenyl) phenyl))-6- (3 -butane) naphthalene

1-fluoro-2- (3,5-diden-4- (3,4-diIL phenyl) phenyl) -6-ethylnaphthalene 1--2--2- (3,5-difluoro-4- (3,4-difluorophenyl) phenyl) -6-propylnaphthalene1-dun-2- (3,5-digas-4- (3,4-difluorophenyl) phenyl) -6- Butadiene 1-fluoro-2- (3,5-difluoro_4- (3,4-difluorophenyl) phenyl) -6-pentaphthalene 1-fluoro-2- (3,5-difluoro- 4- (3,4-Difluorophenyl) phenyl) -6-hexylnaphthalene1-benz-2- (3,5-difluoro-4- (3,4-difluorophenyl) phenyl)- 6-heptaphthalene 1-fluoro-2- (3,5-difluoro-4- (3,4-difluorophenyl) phenyl) -6- (3-butanyl) naphthalene 1-Mao-2- (3,5-difluoro-4- (3,4,5-trifluorophenyl) phenyl) -6-ethylnaphthalene 1-fluoro-2- (3,5-difluoro-4- (3,4 , 5-tri-IL phenyl) phenyl) -6-propylnaphthalene 1-oxo-2- (3,5-difluoro-4- (3,4,5-trifluorophenyl) phenyl) -6-butane Naphthalene 1-fluoro-2- (3,5-difluoro-4_ (3,4,5-tri-II phenyl) phenyl) -6-pentaphthalene 1-gas-2- (3,5-didi- 4- (3,4,5-tritriphenyl) phenyl) -6-hexylnaphthalene 1-gas-2- (3,5-di 4- (3,4,5-trifluorophenyl) phenyl ) -6-heptaphthalene 1-fluoro-2- (3,5-dibenzyl-4- (3,4,5-tri-II phenyl) phenyl) -6- (3-butanyl)

1-fluoro ^ 2- (3,5-digas-4- (4-fluorophenyl) phenyl) -6-ethylnaphthalene1-fluoro-2- (3,5-difluoro-4- (4- Fluorophenyl) phenyl) -6-propylnaphthalene 1-fluoro-2- (3,5-difluoro-4- (4-fluorophenyl) phenyl) -6-butylnaphthalene 1-fluoro-2- ( 3,5-difluoro4- (4-fluorophenyl) phenyl) -6-pentaphthalene 1-fluoro-2- (3,5-difluoro-4- (4-fluorophenyl) phenyl)- 6-Hexaphthalene 1-IL-2- (3,5-difluoro-4- (4-fluorophenyl) phenyl) -6-heptaphthalene

Page 93 528794 V. Description of the invention (91) 1-fluoro-2- (3,5-di 4- (4-phenylphenyl) phenyl) -6- (3-butenyl) naphthalene

1-On-2- (3,5-difluoro-4- (3-Gaphenyl) phenyl) -6-ethylnaphthalene 1-fluoro-2- (3,5-Digas-4- (3- Fluorophenyl) phenyl) -6-propanenaphthalene1-fluoro-2- (3,5-difluoro-4- (3-morphphenyl) phenyl) -6-butylnaphthalene1-fluoro-2- (3 , 5-Dibenzyl-4- (3-Gaphenyl) phenyl) -6-pentaphthalene 1-fluoro-2- (3,5-dibenzyl-4- (3-fluorophenyl) phenyl)- 6-hexylnaphthalene 1-fluoro-2- (3,5-difluoro-4- (3-Itphenyl) phenyl) -6-heptaphthalene 1-fluoro-2- (3,5-di4- ( 3-fluorophenyl) phenyl) -6- (3-butenyl) naphthalene 1-fluoro-2- (3,5-difluoro-4- (3,5-difluorophenyl) phenyl)- 6-Ethylnaphthalene 1-Galine-2- (3,5-difluoro-4- (3,5-difluorophenyl) phenyl) -6-propylnaphthalene 1-fluoro-2- (3,5-di Fluoro 4- (3,5-diphenylphenyl) phenyl) -6-butylene 1-fluoro-2- (3,5-difluoro-4- (3,5-difluorophenyl) phenyl) -6 -pentaphthalene 1-gas-2- (3,5-difluoro-4- (3,5-difluorophenyl) phenyl) -6-hexylnaphthalene 1-fluoro-2- (3,5- Di 4- (3,5-difluorophenyl) phenyl) -6-heptaphthalene 1--2--2- (3,5-difluoro-4- (3,5-difluorophenyl) phenyl) -6- (3-butenyl) naphthalene

1-fluoro-2- (3,5-difluoro-4- (4-chlorophenyl) phenyl) -6-ethylnaphthalene 1-fluoro-2- (3,5-diIt-4- (4- Chlorophenyl) phenyl) -6-propylnaphthalene 1-gas-2- (3,5-difluoro-4- (4-chlorophenyl) phenyl) -6-butylnaphthalene 1-fluoro-2- ( 3,5-Dibenzyl-4- (4-chlorophenyl) phenyl) -6-pentaphthalene 1-fluoro-2- (3,5-difluoro-4- (4-chlorophenyl) phenyl) -6-Hexaphthalene 1-IL-2- (3,5-diH-4- (4-Gaphenyl) phenyl) -6-heptaphthalene

Page 94 528794 V. Description of the invention (92) 1-fluoro-2- (3,5-diH-4- (4-chlorophenyl) phenyl) -6- (3 -butane) naphthalene 1- Gas-2-(3,5-1-iL ~ -2- (3,5-1-fluoro-2- (3,5-1-fluoro-2- (3,5-1-fluoro-2- ( 3, 5-1-Gas-2- (3,5-1-fluoro-2- (3,5-alkenyl) naphthalenefluoro-4- (3-fluoro-4-chlorophenyl) phenyl) -6 -Ethylnaphthalenefluoro-4- (3-June-4_chlorophenyl) phenyl) -6-propynapenefluoro-4- (3-Ga-4-chlorophenyl) phenyl) -6-Butylnaphthalene -4- (3-Dun-4-chlorophenyl) phenyl) -6-pentaphthalene It-4- (3-gas-4-chlorophenyl) phenyl) -6-hexylnaphthalenefluoro-4- ( 3-fluoro-4-chlorophenyl) phenyl) -6-heptaphthonafluoro-4- (3-fluoro-4-chlorophenyl) phenyl) -6- (3-1 1-fluoro-2- ( 3,5-difluoro-4- (3,5-difluoro-4-chlorophenyl) phenyl) -6-ethylnaphthalene 1-fluoro-2- (3,5-difluorene-4- (3, 5-difluoro-4-chlorophenyl) phenyl) -6-propylnaphthalene1-fluoro-2- (3, 5-difluoro-4- (3,5-difluoro-4-chlorophenyl) benzene ) -6-Butylnaphthalene 1-fluoro ^ 2- (3,5-didi-4- (3,5-difluoro-4-chlorophenyl) phenyl) -6-pentaphthalene 1-fluoro-2 -(3,5-diIL-4- (3,5-difluoro-4-chlorophenyl) benzyl) -6-hexylnaphthalene 1-fluoro-2- (3,5-difluoro-4- ( 3,5-difluoro-4-chlorophenyl) phenyl _6 - hept-naphthalene-fluoro-4- (3, 5-difluoro-4-chlorophenyl) benzene naphthalene

1-fluoro-2- (3,5 -diyl) -6- (3 -butyryl)

Page 95 528794 V. Description of the invention (93) 1-fluoro-2-(3,5-difluoro-4-(4-trifluoromethoxyphenyl) phenyl) -6-ethylnaphthalene 1-fluoro-2 -(3,5-difluoro-4- (4-trimethoxymethoxyphenyl) phenyl) -6-propylnaphthalene 1-gas-2- (3,5-difluoro-4- (4-trifluoro Phenoxyphenyl) phenyl) -6-butylene 1-fluoro-2-(3,5 -digas-4- (4-trifluoropyroxyphenyl) phenyl 6-pentaphthalene 1-fluoro-2 -(3, 5-difluoro-4- (4-trifluoromethoxyphenyl) phenyl) -6-hexylnaphthalene 1-fluoro-2- (3, 5-difluoro-4- (4-trifluoro Methoxyphenyl) phenyl) -6-heptaphthalene 1-fluoro-2- (3,5-dibenzyl-4- (4-trifluoromethoxyphenyl) phenyl) -6- (3-butane ) Naphthalene

1-fluoro-2- (3,5-difluoro-4-(3-fluoro-4 -trifluorofluorenoxyphenyl) phenyl) -6-ethylnaphthalene 1-fluoro-2-(3,5-di Fluoro-4-(3-fluoro-4 -tridunmethoxyphenyl) phenyl) -6 -propylnaphthalene 1 -fluoro-2- (3,5-dibenzyl-4- (3- IL-4 -tri Fluoromethoxyphenyl) phenyl) -6-butylnaphthalene 1-fluoro-2-(3,5-difluoro-4- (3-fluoro-4-trifluoromethylphenyl) phenyl) -6- Pentylene naphthalene 1-dun-2- (3,5-difluoro-4- (3-fluoro-4-tri-IL-oxophenyl) phenyl) -6-hexylnaphthalene

1-fluoro-2- (3,5-digas-4- (3-fluoro-4-trifluoromethoxyphenyl) phenyl) -6-heptaphthalene 1-gas-2- (3,5-di Gas-4- (3-fluoro-4 -trifluorofluorenoxyphenyl) phenyl) -6- (3-butenyl) naphthalene 1-fluoro-2- (3,5-digas-4- (3 , 5-Dimorph-4 -trifluoromethoxyphenyl) phenyl) -6-ethylnaphthalene

Page 96 528794 V. Description of the invention (94) 1-fluoro-2- (3,5-difluoro-4- (3,5-difluoro-4 -trifluorofluorenoxyphenyl) phenyl) -6- Propylnaphthalene 1-fluoro-2-(3,5-difluoro-4-(3,5-difluoro-4 -tri-Itmethoxyphenyl) phenyl) -6 -butylnaphthalene 1-fluoro-2- ( 3, 5-difluoro-4- (3, 5-difluoro-4 -trifluoromethoxyphenyl) phenyl) -6-pentaphthalene 1-fluoro-2- (3,5-difluoro-4- (3,5-difluoro-4 -trifluorofluorenoxyphenyl) phenyl) -6-hexylnaphthalene

1-fluoro-2-(3,5-difluoro-4- (3,5-difluoro-4 -tri-ILmethoxyphenyl) phenyl) -6-heptaphthalene 1-fluoro-2- (3, 5-difluoro-4-(3,5-digas-4-trigasmethoxyphenyl) phenyl) -6- (3-butenyl) naphthalene 1-fluoro-2- (3,5-di Fluoro-4- (4-trifluorofluorenoxyphenyl) phenyl) -6-ethylnaphthalene 1-fluoro ^ 2- (3,5-difluoro-4- (4-triILfluorenoxyphenyl) phenyl ) -6-propylnaphthalene 1-fluoro-2-(3,5-difluoro-4- (4-trifluoromethoxyphenyl) phenyl) -6-butylnaphthalene 1-fluoro-2- (3,5 -Difluoro-4- (4-trifluoromethoxyphenyl) phenyl) -6-pentaphthalene 1-fluoro ^ 2- (3,5-difluoro-4- (4-trifluoromethoxyphenyl) Phenyl) -6-hexylnaphthalene 1-fluoro-2-(3,5-difluoro-4- (4-trifluoromethoxyphenyl) phenyl) -6-heptaphthalene

1-fluoro-2-(3,5-difluoro-4-(4-trifluoromethoxyphenyl) phenyl) -6- (3-butenyl) naphthalene 1-fluoro-2- (3,5 -Digas-4- (3-fluoro-4 -difluoromethoxyphenyl) phenyl) _6-ethylnaphthalene 1-fluoro-2- (3, 5-difluoro-4- (3-fluoro-4- Difluoromethoxyphenyl) phenyl) -6-propylnaphthalene

Page 97 528794 V. Description of the invention (95) 1-Ga-2-(3,5-Dibenzyl 4- (3-Fluoro-4 -difluorofluorenyloxyphenyl) phenyl) -6-Butylnaphthalene 1 -Fluoro-2- (3,5-di-11-4- (3-Dun-4 -difluoromethoxyphenyl) phenyl) -6-pentaphthalene 1-fluoro-2- (3,5-difluoro -4- (3- | 1-4-difluoromethoxyphenyl) phenyl) -6-hexylnaphthalene 1-macro-2- (3,5-difluoro-4- (3-fluoro-4 -di Fluoroxophenyl) phenyl) -6-heptaphthalene

1-fluoro-2- (3,5-difluoro-4- (3-gas-4-difluorofluorenyloxyphenyl) phenyl) -δ-0-butenyl) naphthalene 1-fluoro-2- ( 3,5-difluoro ^ 4- (3, 5-difluoro-4 -difluorofluorenyloxyphenyl) phenyl) -6-ethylnaphthalene 1-fluoro-2-(3,5 -digas-4- (3,5-difluoro ^ 4-difluoromethoxyphenyl) phenyl) -6-propylnaphthalene 1-fluoro-2-(3,5-difluoro-4-(3,5-difluoro-4) -Difluoroimethoxyphenyl) phenyl) -6-butylene 1-fluoro-2- (3,5-difluoro-4-(3,5-difluoro-4-difluoromethoxyphenyl) Phenyl) _ 6 -pentaphthalene

1-Fluoro-2- (3,5 -difluoro ^ 4- (3,5-dibenzyl-4 -digasoyloxyphenyl) phenyl) -6-hexylnaphthalene 1-fluoro-2- (3, 5-difluoro-4-(3,5-diIL-4 -diIL oxophenyl) phenyl) -6 • heptaphthalene 1-fluoro-2-(3,5-difluoro-4-(3 , 5 -digas-4-digas oxophenyl) phenyl) -6- (3 -butenyl) naphthalene

Page 98 528794 V. Description of the invention (96) 1-fluoro-2- (3, 5-1-fluoro-2- (3, 5-1-fluoro-2- (3, 5-1-gas-2- (3,5-1-IL-2-(3,5-I -Ga-2- (3,5-1 ~~ Fluoro-2- (3,5-yl) naphthalenefluoro-4-(4-fluoro -4-(4-fluoro-4-(4 -IL- 4-(4-fluoro-4-(4-fluoro-4-(4-fluoro-4- (4-trifluorotolyl) phenyl)- 6-Ethylnaphthalenetrifluorotolyl) phenyl 6-Propernaphthalenetrifluorotolyl) phenyl) -6-Butylnaphthalenetrifluorotolyl) phenyl) -6-Pentaphthalenetrifluoromethylphenyl) phenyl) -6-Hexaphthalenetrifluorotolyl) phenyl) -6-heptaphthalenetriIItolyl) phenyl) -6- (3-butane 1-fluoro-2- (3, 5-difluoro-4- (3-Fluoro-4-trifluorotolyl) phenyl) -6-ethylnaphthalenenaphthalenenaphthalenenaphthalene 1-fluoro-2- (3,5-1-fluoro-2- (3, δ-fluorene-benzyl-2 -(3, 5-1-fluoro-2- (3,5-fluoro-4- (3- IL-4 -trifluorotolyl) phenyl) -6-propane-4- (3-fluoro-4 -Trifluorofluorenyl) phenyl) -6-butylfluoro-4-(3-fluoro-4 -trifluorofluorinyl) phenyl) -6-pentafluoro-4- (3-fluoro-4-tri Gas tolyl) phenyl) -6-hexylnaphthalene 1-fluoro-2- (3, 5-difluoro-4- (3-fluoro-4-trifluorotolyl) phenyl) -6-heptaphthalene 1- Fluoro-2-(3,5-difluoro-4- (3-fluoro-4- Fluorotolyl) phenyl) -δ-O-butenyl) naphthalene 1- Dun-2- (3,5-di-IL-4- (3,5-di-II-4-tri-tolyl) phenyl ) -6-Ethylnaphthalene

Page 99 528794 V. Description of the invention (97) 1-fluoro-2- (3,5-difluoro-4-(3,5-difluoro-4 -trifluorotolyl) phenyl) -6-propane naphthalene 1-Fluoro-2- (3,5-di4- (3,5-difluoro-4-trifluorotolyl) phenyl) -6-buteine 1-fluoro-2- (3,5-difluoro -4- (3,5-difluoro-4 -tridunylphenyl) phenyl) -6-pentaphthalene 1-fluoro-2-(3,5-diden-4- (3,5-difluoro -4-trifluorotolyl) phenyl) -6-hexylnaphthalene1-fluoro-2- (3,5-difluoro-4- (3,5-difluoro-4-trifluorotolyl) phenyl) -6 -heptaphthalene 1-fluoro ^ 2- (3, 5-digas-4- (3,5-di 4 -tri-It tolyl) phenyl) -6- (3 -butane) Cai 1 Fluoro-2- (3,5-difluoro-4-(4-methoxyphenyl) phenyl) -6-ethylnaphthalene 1-gas-2- (3,5-dioxy-4- (4-fluorene Oxyphenyl) phenyl) -6-propylnaphthalene1-fluoro-2- (3,5-diden-4- (4-fluorenyloxyphenyl) phenyl) -6-butylnaphthalene 1-IL-2- (3,5-digas-4- (4-methoxyphenyl) phenyl) -6-pentaphthalene 1-H-2- (3,5-digas-4- (4-methoxyphenyl) Phenyl) -6-hexylnaphthalene 1-fluoro-2-(3,5 -digas-4-(4-methoxyphenyl) phenyl) -6-heptaphthalene 1-fluoro-2- (3,5 -Difluoro-4- (4-methoxyphenyl) phenyl) -6 -(3-Butyl) naphthalene 1-fluoro-2- (3,5-difluoro-4- (3-fluoro-4-methoxyphenyl) phenyl) -6-ethylnaphthalene 1-fluoro-2 -(3,5-difluoro-4-(3-fluoro-4-methoxyphenyl) phenyl) -6-propylnaphthalene 1-gas-2- (3,5-digas-4- (3- 4-Amino-4-phenylphenyl) phenyl) -6-butylnaphthalene 1-IL-2- (3,5-di-4- (3-fluoro-4-methoxyphenyl) phenyl) -6- Pentaphthalene

Page 100 528794 V. Description of the invention (98) 1-fluoro-2- (3,5-difluoroα-4-(3-fluoro-4-oxophenyl) phenyl) -6-hexylnaphthalene 1- Fluoro-2- (3,5-difluoro-4- (3-fluoro-4-methoxyphenyl) phenyl) -6-heptaphthalene 1-fluoro-2- (3,5-difluoro ^ 4- (3-fluoro-4-methoxyphenyl) phenyl) -6- (3-butenyl) naphthalene 1-fluoro-2- (3,5-diIL-4- (3,5-diIL- 4-methoxyphenyl) phenyl) -6-ethylnaphthalene1-fluoro-2- (3,5-diH-4-(3,5-digas-4-oxophenyl) phenyl)- 6-propylnaphthalene

1-fluoro-2- (3,5-difluoroα-4_ (3,5-difluoro-4-methoxyphenyl) phenyl) -6-butylnaphthalene 1-fluoro-2- (3, 5- Difluoro-4- (3, 5-difluoro-4-methoxyphenyl) phenyl) -6-pentaphthalene 1-fluoro-2-(3,5-difluoro-4-(3,5-di Fluoro ^ 4-fluorenylphenyl) phenyl) -6-hexylnaphthalene1-fluoro-2-(3,5-difluoro-4-(3,5-difluoro-4-methoxyphenyl) phenyl ) -6-heptaphthalene 1-gas-2- (3,5-diIL-4- (3,5-difluoro-4-methoxyphenyl) phenyl) -6- (3-butenyl) Naphthalene

1-fluoro-2- (3,5-difluoro-4- (4-dilute propoxyphenyl) phenyl) -6-ethylnaphthalene 1-fluoro-2- (3, 5-difluoro-4- ( 4-allyloxyphenyl) phenyl) -6-propylnaphthalene 1-fluoro-2- (3,5-difluoro-4 (4-dilute propoxyphenyl) phenyl) -6-butylene 1 -Fluoro-2- (3,5-difluoro-4- (4-dilute propoxyphenyl) phenyl) -6-pentaphthalene 1-fluoro-2- (3,5-difluoro-4- (4 -Dilute propoxyphenyl) phenyl) -6-hexylnaphthalene1-fluoro-2- (3,5-diH-4- (4-dilute propoxyphenyl) phenyl) _6_heptaphthalene

Page 528 794

Description of the invention (99) fluorine ~ 2- (3,5-difluoro-4- (4-allyloxyphenyl) phenyl) -6- (3-alkenyl) naphthalene ~ fluoro ~ 2-(3, Difluoro-4- (4-fluorenylphenyl) phenyl) -6 monoethylnaphthalene ~ fluorine ~ 2- (3, 5-difluoro-4- (4-fluorenyl) phenyl) -β-propyl Naphthalene ~ Fluorine ~ 2- (3,5-Difluoro-4-(4-fluorenylphenyl) phenyl) -6-Butylnaphthalene ~ Fluorine ~ 2- (3,5-Difluoro-4- (4-fluorene Phenyl) phenyl) -6-pentaphthalene ~ rat- (3,5-difluoro-4- (4-tolyl) phenyl) -6-hexanaphthalene ~ fluoro- (3, 5-difluoro-4 -(4-fluorenylphenyl) phenyl-6-heptaphthalene ~ rat ~ 2- (3,5-difluoro-4- (4-fluorenylphenyl) phenyl) -6- (3-butanil ) ^ Fluoro-2- (3, 5-difluoro-4_ (4- (3-butenephenyl) phenyl))-6-Ethyl 1-fluoro-2- (3, 5-difluoro-4 -(4- (3-butenephenyl) phenyl))-6-propanzine 1-fluoro-2- (3, 5-difluoro-4- (4- (3-butenephenyl) phenyl )) — 6 — Ding Cai Bu Fluoro-2- (3,5-difluoro-4- (4- (3-butenephenyl) phenyl)) —6 —pent ^ 1-fluoro-2- (3 , 5-difluoro-4- (4- (3-butenephenyl) phenyl))-6-hexane ^ 1-fluoro-2- (3,5-difluoro-4- (4_ (3-butane Allylphenyl) phenyl)) —6 —heptyl H-2- (3,5-diquinol-4- (4- (3-butenyl) phenyl))-6— (3 ^ butenyl) naphthalene ~ [Example 5 ] Synthesis of 1-fluoro-2- (3, 4-difluorophenyl) -6- (trans4-propanecyclohexylnaphthalene) < (5-a) 2- (4-propanecyclohex-1-ene- Synthesis of 1-yl) -6-methoxynaphthalene suspended 22.6 g of magnesium in 30 ml of THF, and 6-bromo-2-phenylbenzene was added dropwise at a rate of about 2 hours at a rate at which the THF can be translated back to the joints. ^ 100mL solution in THF. Followed by stirring] Nai UUg's simmered for 1 hour, this time 丨 hour

Page 102 528794 V. Description of the invention (100) Propanecyclo-130.lgiTHF 5 2 0ml solution. Secondly, t is added with a 20% solution of 10% hydrochloric acid after t. To this was added burned 20000 / organic layer ', and the aqueous layer was extracted with 100 ml of hexane, and the organic layers were combined. Wash with t, a saturated aqueous solution of sodium bicarbonate, and saturated saline, and dry it with anhydrous sodium sulfate. The solvent was distilled off, 280 ml of toluene and 4.0 g of p-toluenesulfonic acid were added, and the mixture was heated under reflux for 3 hours. Allow to cool to room temperature: Wash with water, saturated aqueous sodium bicarbonate solution, and saturated saline solution, and dry with anhydrous sodium sulfate. The solvent was distilled off to obtain g-hexanol 260 g as an oil. The entire amount was dissolved in 800 ml of toluene, and to this was added monohydrate <16-p-toluenesulfonic acid 16 · 1 g, while the distilled water was separated and removed, ^ lj 0- ° C temperature Then heat and stir. After no more water was distilled off, the room temperature was restored, and 300 m 1 of water was added to separate the organic layer. The organic layer was washed with a saturated aqueous solution of sodium hydrogen peroxide, water, and saturated saline, and dried over anhydrous sodium sulfate. The solvent was distilled off to obtain 246 g of a crude product of 2- (4-propanecyclohexane-diluted-based) -6-methoxynaphthalene. (5-b) Synthesis of 2- (trans4-propanecyclohexyl) -6-naphthylnaphthalene gives 2- (4-propcyclohex-1-en-1-yl) -6 as obtained in (5-a) Mono-naphthalene was dissolved in 1,2 L of ethyl acetate in the whole amount, and 4 g of 5% carbon / water (water) was added thereto, and the mixture was stirred under a hydrogen pressure of 4 kg / cm2 in a hot press. After stirring at room temperature for 5 hours, the catalyst was removed by filtration using n SELI ΤΕΠ (a filter aid), and the solvent was distilled off to obtain 2- (4-propanehexyl) -6-methoxynaphthalene. The cis mixture was 260 g. The whole was dissolved in N, N-dimethylformamide (DMF) 1.3L. To this was added 125 g of potassium tributoxide, and the mixture was heated under reflux for 5 hours. It was allowed to cool to room temperature ', and water 200 m 1 was added thereto, and extracted with toluene 200 m 1 twice. Merge organic

Page 103 528794 V. Description of the invention (layer) ’Washed with dilute hydrochloric acid, saturated aqueous sodium hydrogen sulphate solution, water, saturated brine’ and dried with anhydrous sodium hydrate. Gu removed the dissolved coal, purified by Shi Xi gel chromatography (Bengben), and then recrystallized twice by ethanol to obtain 115 g of white crystals of 2- (trans4-propcyclohexyl) -6-naphthylnaphthalene. Synthesis of (5-c) 6- (trans 4-propanecyclohexyl) _2-naphthol For the entire amount of 2- (trans 4-propcyclohexyl) -6-methoxynaphthalene obtained in (I-b), acetic acid was added 70 ml and 70% 48% hydrobromic acid were heated under reflux for 20 hours. After cooling to room temperature, 200 ml of water was added thereto, and extracted twice with 400 ml of toluene. The organic layers were combined, washed sequentially with water and saturated saline, and dried over anhydrous sodium sulfate. The solvent was distilled off to obtain 109 g of 6- (trans 4-propanecyclohexyl) -2-naphthol as white crystals. d) 1 Murine-6- (trans4-propancyclohexyl) -2 -naphthyl synthesis # Make the 6- (trans 4-propancyclohexyl) -2-naphthol obtained in (5-c) dissolved in full amount Dichloromethane 50 0 〇m 1 'Add 7 g of sodium trifluoroxanthoflavin and stir vigorously: = this slow, add bistetrafluoroborate N, "-difluoro-2, 2,- Pyridine 86 · 7g ^ Γ ^ Stir to temperature for 5 hours. Water was added to this, followed by 10% hydrogen and 8K / heydrolyte to decompose the excess fluorinating agent. After the acidity was restored by dilute hydrochloric acid, dv was used to extract the aqueous layer by dichloromethane i〇〇mi and combined. Peel ^ ^ water, saturated brine was washed sequentially, and the crude crystal m.5g obtained by anhydrous sodium sulfate (toluene ;: chemical medium '83g by Shixi gel chromatography) to ^ trans 4-propanecyclohexyl naphthalene Fluoride-6- (trans 4-propylcyclohexyl) -2-naphthol by the full white (iLm lutein acidified 6_ (trans 4-propanecyclohexyl) Cai Ji's synthesis)

Page 104 528794 V. Description of the invention (102) The amount is dissolved in 45.0 ml of dioxane, and 55.3 ml of trifluoromethanesulfonic anhydride is added to make it suspended in it, and it is cooled to 5 it. With vigorous stirring, 54 ml of bite was added dropwise, and then stirred for 1 hour. To this was added water at 100% to stop the reaction and the organic layer was taken in two portions. The aqueous layer was extracted with 100 ml of dichloromethane, and the combined layers were washed successively with dilute hydrochloric acid, a saturated aqueous solution of sodium bicarbonate, water, and saturated salt, and dried over anhydrous sodium sulfate. The solvent was distilled off, and the crude crystals were purified by silica gel chromatography (hexane) to obtain 6 g of white crystals of trifluorosulfonyl ^ trans 4: propanecyclohexyl) naphthalene ~ 2-yl. Person, gas monofluorophenyl) -6- (trans 4-propanecyclohexyl) naphthalene degree ii] ff ™ mi, for which thf can be smoothly refluxed at a temperature of ί / small mouth Japan:% gas + Fill, ™ 7.0g of benzene 3-solution. (5-JU in addition to its excess magnesium 'was added dropwise to the chamber, and at a temperature of 5. °, 2-yl 10 g and _, / fumesanesulfonated 6- (trans 4-propanecyclohexyl) naphthalene were added. Stir ", time and time ~ 0.5 odor Λ (= lin) chain (II) 0.5g &quot; THF 40ml solution. Wash with saline / extract 50ml toluene, extract with water, saturate the surface layer; Method 2 to obtain the fluorine -2- (3,4_ _ * ,,, = refined ethyl ether. Re-crystallized, and the substance seven 85 N ;; 8% of this f) '6- (trans 4 ~ propanecyclohexyl) naphthalene purification can also obtain the following Of compound 1-benz-2- (3,4, benz-2- (3,4, 1-IL-2- (3,4 ~ one messyl radical)) 6- (trans 4-ethylcyclohexyl) Cai Difluorophenyl) -6- (trans 4-butcyclocyclohexyl) naphthalenedifluorophenyl) -6- (trans 4-pentylcyclohexyl) naphthalene

528794 V. Description of the invention (103)

1-fluoro-2- (3,4,5-trifluoro ^ phenyl) -6- (trans 4-ethylcyclohexyl) naphthalene 1-fluoro-2- (3,4,5-trifluorophenyl)- 6- (trans 4-propanecyclohexyl) naphthalene 1-fluoro-2- (3,4,5-trifluorophenyl) -6- (trans 4-butanecyclohexyl) Cai 1-fluoro-2- (3, 4,5-triphenyl) -6- (trans 4-pentylcyclohexyl) naphthalene 1-fluoro-2- (4-fluorophenyl) -6- (trans 4-ethylcyclohexyl) naphthalene 1-fluoro-2 -(4-Itphenyl) -6- (trans4-propcyclohexyl) naphthalene 1-fluoro-2- (4-fluorophenyl) -6- (trans 4-butcyclohexyl) naphthalene 1-fluoro-2 -(4-fluorophenyl) -6- (trans 4-pentylcyclohexyl) naphthalene 1-benz-2- (4-fluorophenyl) -6- (trans 4-hexylcyclohexyl) Cai 1-qi-2 -(4-IIphenyl) -6- (trans4-heptylcyclohexyl) naphthalene 1-fluoro-2- (3-fluorophenyl) -6- (trans4-ethylcyclohexyl) naphthalene 1-fluoro-2 -(3-Fluorophenyl) -6- (trans4-propanecyclohexyl) naphthalene 1-fluoro-2- (3-fluorophenyl) -6- (trans 4-butanecyclohexyl) naphthalene 1-fluoro-2 -(3-Fluorophenyl) -6- (trans 4-pentylcyclohexyl) naphthalene 1-fluoro-2- (3-fluorophenyl) -6- (trans 4-hexylcyclohexyl) Cai 1-fluoro-2 -(3- ILphenyl) -6- (trans 4-heptylcyclohexyl) naphthalene 1-fluoro-2- (3,5-difluorophenyl) -6-(trans 4-ethylcyclohexyl) Cai 1- 2- (3,5-difluorophenyl) -6_ (trans 4-propanecyclohexyl) naphthalene 1- Fluoro-2- (3,5-difluorophenyl) -6- (trans 4-butanecyclohexyl) naphthalene 1-fluoro-2- (3,5-diILphenyl) -6- (trans 4-penta Cyclohexyl) naphthalene 1-fluoro-2- (3,5-difluorophenyl) -6- (trans 4-hexylcyclohexyl) naphthalene 1-benz-2- (3,5-difluorophenyl) -6 -(Trans 4-heptylcyclohexyl) naphthalene 1-fluoro-2-phenyl-6_ (trans 4-ethylcyclohexyl) Cai 1-fluoro-2 ~ phenyl_6- (trans 4-propancyclohexyl)

Page 106 528794 V. Description of the invention (104) 1-fluoro-2 -phenyl-6- (trans 4-butcyclohexyl) naphthalene 1-fluoro-2-phenyl-6- (trans 4-pentylcyclohexyl) CAI 1-Ga-2 -phenyl-6- (trans 4-hexylcyclohexyl) naphthalene 1-fluoro-2 -phenyl-6- (trans 4-heptylcyclohexyl) naphthalene 1-fluoro-2- (4- Chlorophenyl) -6- (trans 4-ethylcyclohexyl) naphthalene 1-fluoro-2- (4-chlorophenyl) -6- (trans 4-propanecyclohexyl) naphthalene 1-fluoro-2- (4- (Chlorophenyl) -6- (trans 4-butcyclohexyl) naphthalene 1-fluoro-2- (4-chlorophenyl) -6- (trans 4-pentylcyclohexyl) naphthalene 1-fluoro-2- (4- Chlorophenyl) -6- (trans4-hexylcyclohexyl) naphthalene 1-fluoro-2- (4-chlorophenyl) -6- (trans 4-heptylcyclohexyl) naphthalene 1-fluoro-2- (3- iL-4-chlorophenyl) -6- (trans 4-ethylcyclohexyl) naphthalene 1-fluoro-2- (3-fluoro-4-chlorophenyl) -6- (trans 4-propanecyclohexyl) naphthalene 1 -Fluoro-2- (3-fluoro-chlorophenyl) -6- (trans 4-butanecyclohexyl) naphthalene 1-town-2- (3-fluoro-4-chlorophenyl) -6- (trans 4- Pentylcyclohexyl) naphthalene 1-fluoro 2- (3-gas-4-chlorophenyl) -6- (trans 4-hexylcyclohexyl) naphthalene 1-fluoro-2- (3-deca-4-chlorophenyl) -6- (trans 4-heptylcyclohexyl) naphthalene 1-fluoro-2- (3,5-difluoro-4-chlorophenyl) -6- (trans 4-ethylcyclohexyl) naphthalene 1-town-2- (3,5-difluoro-4-chlorophenyl) -6- (trans 4-propanecyclohexyl Naphthalene 1-fluoro-2- (3,5-difluoro-4-chlorophenyl) -6- (trans 4-butanecyclohexyl) naphthalene 1-to-2- (3,5-difluoro-4-chloro Phenyl) -6- (trans 4-pentylcyclohexyl) naphthalene 1-fluoro-2- (3,5-difluoro-chlorophenyl) -6- (trans 4-hexylcyclohexyl) naphthalene 1-IL-2 -(3,5 -digas-4-chlorophenyl) -6- (trans 4-heptylcyclohexyl) naphthalene 1-fluoro-2-(4-trifluorofluorenoxyphenyl) -6- (trans 4- Ethylcyclohexyl) naphthalene 1-trifluorofluorenyloxyphenyl) -6- (trans 4-propanecyclohexyl) naphthalene

Page 107 528794 V. Description of the invention (105) 1-Fluoro- (4-trifluoromethoxyphenyl) -6- (trans 4-butanecyclohexyl) naphthalene 1-town-2- (4-trifluoromethoxy Phenyl) -6- (trans 4-pentylcyclohexyl) naphthalene 1-fluoro-2- (4-trifluoromethoxyphenyl) -6- (trans 4-hexylcyclohexyl) naphthalene 1-fluoro ^ 2- ( 4-trifluoromethoxyphenyl) -6- (trans 4-heptylcyclohexyl) naphthalene 1-gas-2- (3-Juni-4 -trifluoromethoxyphenyl) -6- (trans 4-ethylcyclohexyl) Hexyl) naphthalene 1-fluoro-2- (3-fluoro-4 -trifluorofluorenyloxy) -6- (trans 4-propanecyclohexyl) naphthalene 1-fluoro-2- (3-fluoro-4 -trifluoro Phenoxyphenyl) -6- (trans4-butcyclocyclohexyl) naphthalene 1-fluoro-2- (3-fluoro-4 -trifluoromethoxyphenyl) -6- (trans4-pentylcyclohexyl) naphthalene 1 -Fluoro-2- (3-fluoro-trifluoromethoxyphenyl) -6- (trans 4-hexylcyclohexyl) naphthalene 1-fluoro-2-(3-fluoro-4 -tri-IL methoxyphenyl)- 6- (trans 4-heptylcyclohexyl) naphthalene 1-fluoro-2-(3,5-difluoro-4 -trifluorofluorenyloxyphenyl) -6- (trans 4-ethylcyclohexyl) naphthalene 1-fluoro- 2- (3,5 -difluoro-4 -trifluoromethyloxyphenyl) _6- (trans 4-propanecyclohexyl) naphthalene 1-fluoro-2- (3,5-difluoro-4 -trifluoromethoxy Phenyl) -6- (trans 4-butanecyclohexyl) naphthalene 1-fluoro-2- (3,5-difluoro-4-trifluorofluorenyloxyphenyl) -6- (trans 4-pentyl Cyclohexyl) naphthalene 1-It-2- (3,5-difluoro-4 -trifluorofluorenyloxyphenyl) -6- (trans 4-hexylcyclohexyl) naphthalene 1-fluoro-2 (3, 5- Difluoro-4-trifluorofluorenyloxyphenyl) -6- (trans4-heptylcyclohexyl) naphthalene 1-fluoro-2- (4-difluoromethoxyphenyl) -6- (trans4-ethylcyclohexyl) ) Naphthalene 1-gas-2- (4-difluorofluorenyloxyphenyl) -6- (trans 4-propanecyclohexyl) naphthalene

Page 108 528794 V. Description of the invention (106) 1-fluoro-2-(4-difluoromethoxyphenyl) -6- (trans 4-butcyclohexyl) naphthalene 1-fluoro-2-(4-difluoro Methoxyphenyl) -6- (trans 4-pentylcyclohexyl) naphthalene 1-fluoro-2- (4-difluorofluorenyloxyphenyl) -6- (trans 4-hexylcyclohexyl) naphthalene 1-fluoro-2 -(4-Difluorofluorenoxyphenyl) -6- (trans 4-heptylcyclohexyl) naphthalene 1-fluoro-2-(3-fluoro-4 -difluorofluorenyloxyphenyl) -6- (trans 4- Ethylcyclohexyl) naphthalene 1-fluoro-2- (3-fluoro-4-difluorofluorenyloxyphenyl) -6- (trans 4-propanecyclohexyl) naphthalene 1-IL-2-(3-fluoro-4- Difluoro ^ pyroxyphenyl) -6- (trans 4-butcyclohexyl) naphthalene 1-fluoro-2- (3-fluoro-4 -diILmethoxyphenyl) -6- (trans 4-pentylcyclohexyl) ) Naphthalene 1-fluoro-2-(3-gas-4-difluoromethoxyphenyl) -6-(trans 4-hexylcyclohexyl) naphthalene 1-fluoro-2-(3-fluoro-4-difluorofluorene) Oxyphenyl) -6- (trans 4-heptylcyclohexyl) naphthalene 1-gas-2- (3,5-digas-4-difluoromethoxyphenyl) -6- (trans 4-ethylcyclohexyl) Naphthalene 1-Ga-2-(3,5-difluoro-4-difluoromethoxyphenyl) -6- (trans 4-propanecyclohexyl) naphthalene 1-fluoro-2-(3,5-difluoro- 4-difluorofluorenoxyphenyl) -6-(trans 4-butanecyclohexyl) naphthalene 1-fluoro ^ 2- (3,5-difluoro-4- Dioxanyloxyphenyl) -6- (trans 4-pentylcyclohexyl) naphthalene 1-fluoro-2- (3,5-difluoro-4_difluoromethoxyphenyl) -6- (trans 4-hexyl) Cyclohexyl) naphthalene 1-fluoro-2-(3,5-difluoro-4_difluorofluorenyloxyphenyl) -6- (trans 4-heptylcyclohexyl) naphthalene 1-town-2-(4-trifluoro (Phenyl) -6- (trans 4-ethylcyclohexyl) naphthalene 1-fluoro-2-(4-trifluorofluorenyl) -6- (trans 4-propanecyclohexyl) naphthalene

Page 109 528794 V. Description of the invention (107) 1-fluoro-2- (4-trifluorofluorenylphenyl) -6- (trans 4-butanecyclohexyl) naphthalene 1-fluoro-2-(4-trifluorofluorene Phenyl) -6- (trans4-pentylcyclohexyl) Cai 1-Jiu-2- (4-trifluorofluorenylphenyl) -6- (trans4-hexylcyclohexyl) naphthalene1-fluoro-2- (4 -Trifluorofluorenyl) -6- (trans 4-heptylcyclohexyl) naphthalene 1-fluoro-2- (3-fluoro-4 -tri-IL tolyl) -6- (trans 4-ethylcyclohexyl) naphthalene 1- Fluoro-2-(3-fluoro-4 -tridecyltolyl) -6-(trans 4-propanecyclohexyl) naphthalene 1-fluoro-2- (3-fluoro-4-trifluorotolyl) -6- ( Trans 4-butcyclocyclohexyl) naphthalene 1-fluoro-2- (3-fluoro-4 -trifluoro i-phenyl) -6- (trans 4-pentcyclohexyl) naphthalene 1-fluoro-2- (3-fluoro -4 -trifluorofluorenyl) -6- (trans4-hexylcyclohexyl) qin 1-fluoro-2- (3-fluoro * -4 -trifluorotolyl) -6-(trans 4-heptylcyclohexyl) ) Naphthalene 1-fluoro-2- (3,5-difluoro-4 -tri-Ittolyl) -6-(trans 4-ethylcyclohexyl) naphthalene 1-fluoro-2- (3,5-difluoro-4 -Trifluorofluorenyl) -6- (trans4-propancyclohexyl) naphthalene 1-fluoro-2- (3,5-bis4-trifluorofluorenyl) -6- (trans4-butcyclocyclohexyl) Naphthalene 1-fluoro ^ -2- (3,5 -difluoro-4 -tri-Ittolyl) -6- (trans 4-pentylcyclohexyl) naphthyl-2- (3,5-difluoro-4-trifluorotolyl) -6- (trans 4-hexylcyclohexyl) naphthalene 1-benzyl-2-(3,5-difluoro ^ 4-trifluorotolyl) -6 -(Trans 4-heptylcyclohexyl) naphthalene 1-fluoro-2-(4-fluorenyloxyphenyl) -6-(trans 4-ethylcyclohexyl) naphthalene 1-fluoro-2-(4-fluorenyloxyphenyl) -6- (trans 4-propanecyclohexyl) naphthalene

Page 110 528794 V. Description of the invention (108)

1-fluoro-2- (4-fluorenylphenyl) -6- (trans 4-butcyclohexyl) naphthalene 1-fluoro-2- (4-methoxyphenyl) -6- (trans 4-pentylcyclohexyl ) Naphthalene 1-fluoro-2- (4-fluorenyloxyphenyl) -6- (trans 4-hexylcyclohexyl) naphthalene 1-den-2- (4-fluorenyloxy) -6- (trans 4-heptyl Cyclohexyl) naphthalene 1-fluoro-2- (3-fluoro-4-fluorenyloxyphenyl) -6- (trans 4-ethylcyclohexyl) naphthalene 1-fluoro-2- (3-fluoro-4-fluorenyloxybenzene) ) -6- (trans 4-propanecyclohexyl) naphthalene l- | L-2- (3-fluoro-4-methoxyphenyl) -6- (trans 4-butanecyclohexyl) naphthalene 1-fluoro-2 -(3-fluoro-4-methoxyphenyl) -6-(trans 4-pentylcyclohexyl) naphthalene 1-gas-2- (3-fluoro-4-oxophenyl) -6- (trans 4- Hexylcyclohexyl) naphthalene 1-fluoro-2- (3-fluoro-4-fluorenyloxyphenyl) -6- (trans 4-heptylcyclohexyl) naphthalene 1-gas-2- (3,5-diden-4 -Fluorenylphenyl) -6- (trans4-ethylcyclohexyl) naphthalene 1-fluoro-2-(3,5-digas-4-methoxyphenyl) -6- (trans4-propanecyclohexyl) Naphthalene 1-fluoro-2- (3,5-diH-fluorenyloxyphenyl) -6- (trans 4-butcyclohexyl) naphthalene 1-fluoro-2- (3, 5-difluoro-4-fluorenyloxy Phenyl) -6 trans 4-pentylcyclohexyl) naphthalene 1-fluoro-2- (3,5-difluoro-4-methoxyphenyl) -6-(trans 4-hexylcyclohexyl) naphthalene 1-gas- 2-(3,5 -digas-4-methoxyphenyl) -6-(trans 4- Cyclohexyl) naphthalene 1-fluoro-2- (4-allyloxyphenyl) -6- (trans 4-ethylcyclohexyl) naphthalene 1-fluoro-2- (4-allyloxyphenyl) -6- ( Trans 4-propanecyclohexyl) naphthalene 1-fluoro-2- (4-allyloxyphenyl) -6- (trans 4-butanecyclohexyl) naphthalene 1-fluoro-2- (4-allyloxyphenyl) -6- (trans 4-pentylcyclohexyl) naphthalene 1-fluoro-2- (4-allyloxyphenyl) -6- (trans 4-hexylcyclohexyl) naphthalene 1-fluoro-2- (4-dilute propane Oxyphenyl) -6- (trans 4-heptylcyclohexyl) naphthalene 1-gas-2- (4-fluorenylphenyl) -6- (trans 4-ethylcyclohexyl) naphthalene 1-fluoro-2- (4- Tolyl) -6- (trans4-propanecyclohexyl) naphthalene

Page 111 528794 V. Description of the invention (109) 1-fluoro-2- (4-tolyl) -6- (trans 4-butanecyclohexyl) naphthalene 1-fluoro-2- (4-tolyl) -6- (Trans 4-pentylcyclohexyl) naphthalene 1-fluoro-2- (4-tolyl) -6- (trans 4-hexylcyclohexyl) naphthalene 1-gas-2- (4-fluorenyl) -6- ( Trans 4-heptylcyclohexyl) naphthalene 1-I-2- [4- (3 -butylfluorenyl) phenyl] -6- (trans 4-ethylcyclohexyl) naphthalene 1-fluoro-2- [4- (3 -Butenyl) phenyl] -6- (trans4-propcyclohexyl) naphthalene 1-fluoro-2- [4- (3 -butenyl) phenyl] -6- (trans 4-butcyclohexyl) Naphthalene 1-fluoro-2- [4- (3 -butenyl) phenyl] -6- (trans 4-pentylcyclohexyl) naphthalene 1-gas-2- [4- (3 -butenyl) phenyl]- 6- (trans 4-hexylcyclohexyl) naphthalene 1- 2- [4- (3 -butenyl) phenyl] -6- (trans 4-heptylcyclohexyl) qin [Example 6] 1_ 2- (3 Synthesis of 4,4-Digas) phenyl-6- [2- (trans4-propanecyclohexyl) ethyl] naphthalene In Example 5, except that trans 4-propanecyclohexaneacetaldehyde was used instead of 4-propane Cyclohexanone was carried out in the same manner except that the isomerization in (5 -b) was not performed to obtain 1-fluoro-2-(3,4-difluorophenyl) -6- [2- (trans4- Propylcyclohexyl) ethyl] white crystals of naphthalene. The following compounds can also be obtained. 1-Ga-2- (3,4-difluorophenyl) -6- [2- (trans 4-ethylcyclohexyl) ethyl] naphthalene 1-Ga-2- (3,4-difluorophenyl) -6- [2- (trans 4-butcyclohexyl) ethyl] naphthalene 1-gas-2- (3,4-digasphenyl) -6- [2- (trans 4-pentylcyclohexyl) ethyl ] Naphthalene 1-IL-2- (3,4,5-trifluorophenyl) -6- [2- (trans 4-ethylcyclohexyl) ethyl] naphthalene 1-jim-2- (3,4,5 -Trifluorophenyl) -6- [2- (trans4-propanecyclohexyl) ethyl] naphthalene

Page 112 528794 V. Description of the invention (110) 1-fluoro-2- (3,4,5-trifluorophenyl) -6- [2- (trans 4-butcyclohexyl) ethyl] naphthalene 1-fluoro -2-(3, 4, 5-trifluorophenyl) -6- [2- (trans4-pentylcyclohexyl) ethyl] naphthalene 1-benz-2- (4-fluorophenyl) -6- [ 2- (trans 4-ethylcyclohexyl) ethyl] naphthalene 1-fluoro-2- (4-fluorophenyl) -6- [2- (trans 4-propanecyclohexyl) ethyl] naphthalene 1-fluoro-2 -(4-fluorophenyl) -6- [2- (trans 4-butcyclohexyl) ethyl] naphthalene 1-fluoro-2- (4- Itphenyl) -6- [2- (trans 4-pentyl Cyclohexyl) ethyl] naphthalene 1-gas-2- (4-gasphenyl) -6- [2- (trans 4-hexylcyclohexyl) ethyl] Cai 1-fluoro ^ 2- (4-fluorophenyl ) -6- [2- (trans 4-heptylcyclohexyl) ethyl] naphthalene 1-fluoro-2- (3-fluorophenyl) -6- [2- (trans 4-ethylcyclohexyl) ethyl] naphthalene 1-fluoro-2- (3-fluorophenyl) -6- [2- (trans 4-propanecyclohexyl) ethyl] naphthalene 1-fluoro-2- (3-fluorophenyl) -6- [2- (Trans 4-butylcyclohexyl) ethyl] naphthalene 1-gas-2- (3-fluorophenyl 6- [2- (trans 4-pentylcyclohexyl) ethyl] naphthalene 1-dun-2- (3- Fluorophenyl) -6- [2- (trans4-hexylcyclohexyl) ethyl] naphthalene 1-benz-2- (3-fluorophenyl) -6- [2- (trans4-heptylcyclohexyl) ethyl Yl] naphthalene 1-5 -difluorophenyl) -6- [2- (trans 4-ethylcyclohexyl) ethyl] naphthalene 1-It-2- (3 5 -diIIphenyl) -6- [2- (trans4-propancyclohexyl) ethyl] naphthalene 1-IL-2- (3,5-diItphenyl) -6- [2- (trans-4 -Butylcyclohexyl) ethyl] naphthalene 1-fluoro-2- (3,5-difluorophenyl) -6- [2- (trans 4-pentylcyclohexyl) ethyl] naphthalene 1-fluoro-2- ( 3,5-difluorophenyl) -6- [2- (trans4-hexylcyclohexyl) ethyl] naphthalene 1-fluoro-2- (3,5-difluoro1phenyl) -6- [2- (Trans 4-heptylcyclohexyl) ethyl] naphthalene 1-gas-2_benzyl-6- [2- (trans 4-ethylcyclohexyl) ethyl] Cai 1-fluoro-2 -phenyl_6- [ 2- (trans4-propanecyclohexyl) ethyl] Cai

Page 113 528794 V. Description of the invention (111) l-benzyl-2-phenyl-6- [2- (trans 4-butcyclohexyl) ethyl] Cai 1-qi-2 -phenyl-6- [2 -(Trans 4-pentylcyclohexyl) ethyl] Cai 1-benz-2-phenyl-6- [2- (trans 4-hexylcyclohexyl) ethyl] Cai 1-fluoro-2-phenyl-6- [2- (trans 4-heptylcyclohexyl) ethyl] naphthalene 1-gas-2- (4-chlorophenyl) -6- [2- (trans 4-ethylcyclohexyl) ethyl] naphthalene 1-fluoro ^ 2- (4-chlorophenyl) -6- [2- (trans 4-propanecyclohexyl) ethyl] naphthalene 1-fluoro-2- (4-chlorophenyl) -6- [2- (trans 4- Butylcyclohexyl) ethyl] naphthalene 1-fluoro-2- (4-chlorophenyl) -6- [2- (trans 4-pentylcyclohexyl) ethyl] naphthalene 1-dun-2- (4-chlorobenzene ) -6- [2- (trans 4-hexylcyclohexyl) ethyl] naphthalene 1-IL-2- (4-chlorophenyl) -6- [2- (trans 4-heptylcyclohexyl) ethyl] Naphthalene 1-fluoro-2-(3-fluoro_4-chlorophenyl) -6- [2- (trans 4-ethylcyclohexyl) ethyl] Naphthalene 1-dun-2- (3- 4-chlorophenyl )-6- [2- (trans4-propancyclohexyl) ethyl] naphthalene 1-fluoro-2- (3-fluoro-4-chlorophenyl) -6- [2- (trans 4-butcyclohexyl) Ethyl] naphthalene 1-fluoro-2- (3-fluoro-4-chlorophenyl) -6- [2- (trans 4-pentylcyclohexyl) ethyl] naphthalene 1-fluoro ^ 2- (3-fluoro- 4-chlorophenyl) -6- [2- (trans4-hexylcyclohexyl) ethyl] naphthalene 1-fluoro-2- (3-fluoro-4-chlorobenzene ) -6- [2- (trans-4 - heptyl cyclohexyl) ethyl] naphthalene 1-5-- two 4-chlorophenyl) -6- [2- (trans-4- ethyl-cyclohexyl) ethyl] naphthalene

Page 114 528794 V. Description of the invention (112) 1-Dun-2- (3,5-difluoro-4-chlorophenyl) -6- [2- (trans4-propcyclohexyl) ethyl] naphthalene 1 -Fluoro-2- (3,5-difluoro-4_chlorophenyl) -6_ [2- (trans 4-butanecyclohexyl) ethyl] naphthalene 1-town-2- (3,5-digas- 4-chlorophenyl) -6- [2- (trans 4-pentylcyclohexyl) ethyl] naphthalene 1-fluoro-2- (3,5-difluoro-4_chlorophenyl) -6- [2- (Trans 4-hexylcyclohexyl) ethyl] naphthalene 1-gas-2- (3,5-difluoro-4_chlorophenyl) -6- [2- (trans 4-heptylcyclohexyl) ethyl] naphthalene 1-fluoro-2- (4-trifluoromethoxyphenyl) -6- [2- (trans 4-ethylcyclohexyl) ethyl] naphthalene 1-fluoro-2-(4-trifluorofluorenyloxyphenyl) -6- [2- (trans4-propanecyclohexyl) ethyl] naphthalene 1-gas-2- (4-trifluoromethoxyphenyl)-6-[2- (trans 4-butcyclocyclohexyl) ethyl ] Naphthalene 1-fluoro-2- (4-trifluorofluorenyloxyphenyl) -6- [2- (trans 4-pentylcyclohexyl) ethyl] Naphthalene 1-fluoro-2-(4-trifluoroimethoxy Phenyl) -6-[2- (trans4-hexylcyclohexyl) ethyl] naphthalene 1-gas-2- (4-trigasmethoxymethoxyphenyl) -6- [2- (trans 4-heptylcyclohexyl) ) Ethyl] naphthalene 1-fluoro- (3-fluoro-4 -tri-ILmethoxyphenyl) -6- [2- (trans 4-ethylcyclohexyl) ethyl] naphthalene

528794 V. Description of the invention (113) 1- 1 ^ -2- (3- IL-4 -trifluoromethoxyphenyl) -6- [2- (trans 4-propcyclohexyl) ethyl] naphthalene 1-gas -2- (3-fluoro-4-trifluoromethoxyphenyl) -6- [2- (trans 4-butanecyclohexyl) ethyl] naphthalene 1-fluoro ^ 2- (3-gas-4 -tridecane Methoxyphenyl) -6- [2- (trans 4-pentylcyclohexyl) ethyl] qin 1- 2- (3-fluoro-4-trifluoromethoxyphenyl) -6- [2-(trans-4 -Hexylcyclohexyl) ethyl] naphthalene 1-benzyl-2- (3-IL-4 -tris-methoxymethoxyphenyl) -6- [2- (trans 4-heptylcyclohexyl) ethyl] naphthalene 1-gas -2- (3,5-difluoro-4 -trifluoromethoxyphenyl) -6- [2- (trans 4-ethylcyclohexyl) ethyl] naphthalene 1-fluoro-2- (3,5-di IL-4 -trifluoromethoxyphenyl) -6-[2- (trans 4-propanecyclohexyl) ethyl] naphthalene 1-fluoro-2- (3,5 -digas-4 -trifluoromethoxybenzene Yl) -6- [2- (trans4-butcyclohexyl) ethyl] naphthalene I-fluoro-2- (3,5-diphenyl-4-trifluoro1oxoxyphenyl) -6- [2- (Trans 4-pentylcyclohexyl) ethyl] naphthalene 1-fluoro-2- (3,5-difluoro-4 -tridunmethoxyphenyl) -6- [2- (trans 4-hexylcyclohexyl) ethyl Yl] naphthalene 1-benz-2- (3,5-difluoro-4 -trifluoromethoxyphenyl) -6-[2- (trans 4-heptylcyclohexyl) ethyl] qin 1-qi-2- (4-DiIL oxophenyl) -6-[2- ( Trans 4-ethylcyclohexyl) ethyl] naphthalene

Page 116 528794 V. Description of the invention (114) 1- IL-2- (4-digasmethoxymethoxyphenyl 6- [2- (trans 4-propcyclohexyl) ethyl] naphthalene I-1-2- ( 4-difluoromethoxyphenyl) -6- [2- (trans 4-butanecyclohexyl) ethyl] naphthalene 1-fluoro-2-(4-difluoromethoxyphenyl) -6- [2- ( Trans 4-pentylcyclohexyl) ethyl] naphthalene 1-fluoro-2- (4-difluoromethoxyphenyl) -6- [2- (trans 4-hexylcyclohexyl) ethyl] naphthalene 1-just-2 -(4-difluoromethoxyphenyl) -6- [2- (trans 4-heptylcyclohexyl) ethyl] Tsai 1-fluoro-2- (3- I-4 -difluoroi-methoxyphenyl) -6- [2- (trans 4-ethylcyclohexyl) ethyl] naphthalene 1-fluoro-2- (3-fluoro-4 -difluoromethoxyphenyl) -6-[2- (trans 4-propane ring Hexyl) ethyl] naphthalene 1-fluoro-2-(3-gas-4 -difluorofluorenoxyphenyl) -6- [2- (trans4-butcyclocyclohexyl) ethyl] naphthalene 1-fluoro-2- (3-Fluoro-4-difluorofluorenyloxy) -6- [2- (trans 4-pentylcyclohexyl) ethyl] naphthalene 1-dun-2- (3-fluoro-4-difluoromethoxybenzene Group) -6- [2- (trans4-hexylcyclohexyl) ethyl] qin 1-fluoro-2- (3-gas-4 -difluoromethoxyphenyl) -6- [2- (trans 4- Heptylcyclohexyl) ethyl] naphthalene 1-fluoro-2- (3,5-difluoro-4 -difluoro i-oxophenyl) -6- [2- (trans 4-ethylcyclohexyl) ethyl] naphthalene

Page 117 528794 V. Description of the invention (115) 1-Jiu-2- (3,5-difluoro-4-dioxanyloxyphenyl) -6- [2- (trans4-propanecyclohexyl) ethyl ] Naphthalene 1-fluoro-2- (3,5-difluoro-4 -difluorofluorenoxyphenyl) -6- [2- (trans 4-butcyclohexyl) ethyl] naphthalene 1-fluoro-2- ( 3,5-difluoro-4-difluorofluorenoxyphenyl) -6- [2- (trans 4-pentylcyclohexyl) ethyl] naphthalene 1-fluoro-2-(3,5-difluoro-4- Difluoroimethoxyphenyl) -6- [2- (trans4-hexylcyclohexyl) ethyl] naphthalene 1-fluoro ^ 2- (3,5-diIL-4 -difluoromethoxyphenyl)- 6-[2- (trans4-heptylcyclohexyl) ethyl] naphthalene 1-dun-2- (4-trifluorofluorenylphenyl) -6- [2- (trans4-ethylcyclohexyl) ethyl] naphthalene 1-fluoro-2- (4-trifluoroi-tolyl 6- [2- (trans 4-propanecyclohexyl) ethyl] naphthalene 1-H-2- (4-trifluorofluorenyl) -6- [ 2- (trans 4-butcyclocyclohexyl) ethyl] naphthalene 1-fluoro-2- (4-trifluorofluorenylphenyl 6- [2- (trans 4-pentcyclohexyl) ethyl] naphthalene 1-benz-2 -(4-trifluorofluorenyl) -6- [2- (trans 4-hexylcyclohexyl) ethyl] naphthalene 1-fluoro-2- (4-trifluorofluorenyl) -6-[2- ( Trans 4-heptylcyclohexyl) ethyl] naphthalene 1-gas-2- (3-fluoro-4-trigastolyl) -6- [2- (trans 4-ethylcyclohexyl) ethyl] naphthalene 1-morphology -2- (3-fluoro-4 -three gases Tolyl) -6- [2- (trans4-propanecyclohexyl) ethyl] naphthalene 1-said-2- (3-fluoro-4 -trifluorotolyl) -6- [2- (trans 4-but Cyclohexyl) ethyl] naphthalene 1-fluoro-2- (3-gas-4 -trifluoroi-tolyl) -6- [2- (trans 4-pentylcyclohexyl) ethyl] naphthalene

Page 118 528794 V. Description of the invention (116) 1-fluoro-2- (3-trifluorotolyl) -6- [2- (trans4-hexylcyclohexyl) ethyl] naphthalene 1-fluoro-2- ( 3-fluoro-4-trifluorotolyl) -6- [2- (trans 4-heptylcyclohexyl) ethyl] naphthalene 1-fluoro-2- (3,5-difluoro ^ 4-trifluorofluorenylphenyl ) -6-[2- (trans4-Ethylcyclohexyl) ethyl] qin 1-fluoro-2-(3,5-difluoro-4 -trifluorotolyl) -6-[2-(trans 4- Propylcyclohexyl) ethyl] naphthalene 1-bromo-2-(3,5-difluoro-4 -trifluorofluorenylphenyl) -6- [2-(trans 4 -butylcyclohexyl) ethyl] naphthalene 1- Fluoro-2-(3,5-difluoro-4 -trifluorotolyl) -6- [2- (trans 4-pentylcyclohexyl) ethyl] naphthalene 1- Dun-2- (3,5-difluoro -4 -Three gas tolyl) -6-[2- (trans 4-hexylcyclohexyl) ethyl] naphthalene 1-fluoro-2- (3,5-difluoro-4 -tri-It tolyl) _6-[ 2- (trans 4-heptylcyclohexyl) ethyl] naphthalene 1-benzyl-2- (4-fluorenyloxyphenyl) -6- [2- (trans 4-ethylcyclohexyl) ethyl] naphthalene 1-fluoro- 2- (4-fluorenoxyphenyl) -6- [2- (trans 4-propancyclohexyl) ethyl] naphthalene 1-fluoro-2- (4-fluorenoxyphenyl) -6- [2- (trans 4-Butylcyclohexyl) ethyl] Cai 1-den-2-(4-fluorenyloxy) -6- [2- (trans 4-pentylcyclohexyl) ethyl] naphthalene 1-fluoro ^ 2- (4 -Fluorenylphenyl) -6-[2- (trans4-hexylcyclohexyl) ethyl] naphthalene 1-fluoro-2- (4-fluorenyloxyphenyl) -6- [2- (trans4-heptyl ring) Hexyl) ethyl] naphthalene 1-fluoro-2-(3-gas-4-methoxyphenyl) -6- [2- (trans4-ethylcyclohexyl) ethyl] naphthalene

Page 119 528794 V. Description of the invention (117) 1-Fluoro-2- (3-fluoro-4-oxophenyl) -6- [2- (trans4-propanehexyl) ethyl] naphthalene 1-fluoro -2- (3-fluoro-4-fluorenyloxyphenyl) -6- [2- (trans 4-butanecyclohexyl) ethyl] naphthalene 1-gas-2- (3 ~ · qi-4-fluorenoxybenzene -)-6- [2- (trans 4-fluorenylcyclohexyl) ethyl] naphthalene 1-fluoro-2- (3-gas-4-methoxyphenyl) -6- [2- (trans 4-hexylcyclohexyl) ) Ethyl] naphthalene

1-Ga-2- (3-fluoro ^ -4-methoxyphenyl) -6- [2- (trans 4-heptylcyclohexyl) ethyl] qin 1-fluoro-2- (3,5-difluoro Mono 4-methoxyphenyl) -6- [2- (trans 4-ethylcyclohexyl) ethyl] qin 1-fluoro-2-(3,5 -digas-4-methoxyphenyl) -6- [2- (trans 4-propanecyclohexyl) ethyl] naphthalene 1-fluoro-2- (3,5-difluoro-4-methoxyphenyl) -6- [2- (trans-butylcyclohexyl) ethyl ] Qin 1-fluoro 2-(3,5-diIL-4-methoxyphenyl) -6-[2- (trans 4-pentylcyclohexyl) ethyl] naphthalene

1-fluoro ^ 2- (3,5-di-4-methoxyphenyl) -6- [2- (trans 4-hexylcyclohexyl) ethyl] qin 1-fluoro-2-(3,5-di Fluoro-4-fluorenoxyphenyl) -6- [2- (trans 4-heptylcyclohexyl) ethyl] naphthalene 1-fluoro-2- (4-dilute propoxyphenyl) -6- [2- (trans 4-Ethylcyclohexyl) ethyl] naphthalene 1-fluoro-2- (4- roasted propoxyphenyl) -6- [2- (trans 4-propanehexyl) ethyl] naphthalene

Page 120 528794 V. Description of the invention (118)

Fluoro-2- (4-dilute propoxyphenyl) -6- [2- (trans 4-butanecyclohexyl) ethyl] qin 1-fluoro-2- (4-dilute propoxyphenyl) -6- [ 2- (trans 4-pentylcyclohexyl) ethyl] naphthalene 1-fluoro-2- (4-dilute propoxyphenyl) -6- [2- (trans 4-hexylcyclohexyl) ethyl] naphthalene 1-fluoro -2- (4- Dilute propoxyphenyl) -6- [2- (trans 4-heptylcyclohexyl) ethyl] naphthalene 1-fluoro-2- (4-fluorenyl) -6- [2- ( Trans 4-ethylcyclohexyl) ethyl] cai 1-fluoro-2- (4-fluorenylphenyl 6- [2- (trans 4-propancyclohexyl) ethyl] naphthalene 1-fluoro-2- (4-toluene ) -6- [2- (trans 4-butcyclohexyl) ethyl] naphthalene 1-fluoro-2- (4-tolyl) -6- [2- (trans 4-pentcyclohexyl) ethyl] naphthalene 1-fluoro-2- (4-tolyl) -6- [2- (trans 4-hexylcyclohexyl) ethyl] naphthalene 1-fluoro-2- (4-tolyl) -6- [2- (trans 4-heptylcyclohexyl) ethyl] naphthalene 1-fluoro-2- [4- (3-butenyl) phenyl] -6- [2- (trans 4-ethylcyclohexyl) ethyl] naphthalene 1-said -2- [4- (3 -butenyl) phenyl] -6- [2- (trans 4-propancyclohexyl) ethyl] naphthalene 1-fluoro ^ 2- [4- (3 -butenyl) Phenyl]-6- [2- (trans 4-butanecyclohexyl) ethyl] naphthalene 1-fluoroi-2_ [4- (3 -butenyl) phenyl] -6- [2- (trans 4- Cyclohexyl) ethyl] naphthalene

1-fluoro-2- [4- (3-butanyl) phenyl] -6- [2- (trans 4-hexylcyclohexyl) ethyl] naphthalene 1-fluoro ^ 2_ [4- (3-butane ) Phenyl] -6- [2- (trans 4-heptylcyclohexyl) ethyl] naphthalene 1-IL-2- (3,4-difluorophenyl) -6- [2- (4-ethylbenzene (Yl) ethyl] naphthalene 1-town-2- (3,4-difluorophenyl) -6- [2- (4-butylene) ethyl] naphthalene

Page 121 528794 V. Description of the Invention (119)

1-fluoro-2- (3,4-difluorophenyl) -6- [2- (4-pentylphenyl) ethyl] naphthalene 1-town-2- (3,4,5-trifluorophenyl ) -6- [2- (4-ethylphenyl) ethyl] naphthalene 1-gas-2- (3,4,5-trifluorophenyl) -6- [2- (4-propylphenyl) ethyl Yl] naphthalene 1-fluoro_2- (3,4,5-trifluoro1phenyl) -6- [2- (4-butylphenyl) ethyl] naphthalene 1-fluoro ^ 2- (3,4, 5-trifluorophenyl) -6- [2- (4-pentylphenyl) ethyl] naphthalene 1-fluoro-2- (4-fluorophenyl) -6- [2- (4-ethylphenyl) Ethyl] naphthalene 1-fluoro-2- (4-fluorophenyl) -6- [2- (4-propylphenyl) ethyl] naphthalene 1-fluoro-2- (4-fluorophenyl) -6- [2- (4-Butylphenyl) ethyl] naphthalene 1-fluoro-2- (4-fluorophenyl) -6- [2- (4-pentylphenyl) ethyl] naphthalene 1-fluoro-2- (4-fluorophenyl) -6- [2- (4-hexylphenyl) ethyl] naphthalene 1-fluoro-2- (4-fluorophenyl) -6- [2- (4-heptylphenyl) Ethyl] naphthalene 1-It -2- (3-Gaphenyl) -6- [2- (4-ethylphenyl) ethyl] naphthalene 1-fluoro-2- (3-fluorophenyl) -6- [2- (4-propylphenyl) ethyl] naphthalene 1-fluoro-2- (3-fluorophenyl) -6- [2- (4-butylene) ethyl] naphthalene 1-fluoro-2- (3-Gaphenyl) -6- [2- (4-pentylphenyl) ethyl] naphthalene 1-fluoro-2- (3-fluorophenyl) -6- [2- (4-hexylphenyl) Ethyl] naphthalene 1-fluoro-2- (3-gasphenyl) -6- [2- (4-heptylphenyl) Ethyl] naphthalene 1-fluoro-2- (3,5-difluorophenyl) -6-[2- (4-ethylphenyl) ethyl] naphthalene 1-fluoro-2- (3,5-difluoro Phenyl) -6- [2- (4-propylphenyl) ethyl] naphthalene 1-fluoro-2- (3,5-diILphenyl) -6- [2- (4-butylphenyl) ethyl Yl] naphthalene 1-said-2- (3,5-difluorophenyl) -6_ [2- (4-pentylphenyl) ethyl] naphthalene 1-5-diphenyl) -6- [2- ( 4-hexylphenyl) ethyl] naphthalene 1-fluoro-2- (3, 5-difluorophenyl) -6- [2- (4-heptylphenyl) ethyl] naphthalene 1-It-2 -benzene -6- [2- (4-ethylphenyl) ethyl] naphthalene

Page 122 528794 V. Description of the invention (120)

I -Ga-2-phenyl-6- [2- (4-propylphenyl) ethyl] naphthalene 1-Di-2-phenyl-6- [2- (4-butylphenyl) ethyl] naphthalene 1-fluoro-2-phenyl-6- [2- (4-pentylphenyl) ethyl] naphthalene 1-fluoro-2-phenyl-6- [2- (4-hexylphenyl) ethyl] naphthalene 1-Like-2 -phenyl-6- [2- (4-heptylphenyl) ethyl] naphthalene 1-fluoro-2- (4-chlorophenyl) -6- [2- (4-ethylphenyl ) Ethyl] naphthalene 1-gas-2- (4-chlorophenyl) -6- [2- (4-propylphenyl) ethyl] naphthalene 1-fluoro-2- (4-chlorophenyl) -6 -[2- (4-Butylphenyl) ethyl] naphthalene 1-fluoro-2- (4-chlorophenyl) -6- [2- (4-pentylphenyl) ethyl] naphthalene 1-fluoro-2 -(4-chlorophenyl) -6- [2- (4-hexylphenyl) ethyl] naphthalene 1-fluoro-2- (4-chlorophenyl) -6- [2- (4-heptylphenyl) ) Ethyl] naphthalene 1-fluoro-2- (3- 4-chlorophenyl) -6- [2- (4-ethylphenyl) ethyl] naphthalene 1-fluoro-2- (3-fluoro-4- Chlorophenyl) -6- [2- (4-propylphenyl) ethyl] naphthalene 1-fluoro-2- (3-fluoro-4-chlorophenyl) -6- [2- (4-butylphenyl ) Ethyl] naphthalene 1-fluoro-2- (3-fluoro-4-chlorophenyl) -6- [2- (4-pentylphenyl) ethyl] naphthalene 1-lt-2- (3- 4- Chlorophenyl) -6- [2- (4-hexylphenyl) ethyl] naphthalene

1-fluoro-2- (3-Ga-4-chlorophenyl) -6- [2- (4-heptylphenyl) ethyl] naphthalene 1-fluoro-2- (3,5-difluoro-4- Chlorophenyl) -6- [2- (4-ethylphenyl) ethyl] naphthalene 1-fluoro-2- (3,5-difluoro-4-chlorophenyl) -6- [2- (4_ Propylphenyl) ethyl] naphthalene 1-fluoro-2- (3,5-digas-4-chlorophenyl) -6- [2- (4-butylphenyl) ethyl] naphthalene 1-fluoro-2 -(3,5-difluoro-4-chlorophenyl) -6- [2- (4-pentylphenyl) ethyl]

Page 123 528794 V. Description of the invention (121) Naphthalene 1-fluoro 2- (3,5-digas-4-chlorophenyl) -6- [2- (4-hexylphenyl) ethyl] Naphthalene 1- Fluoro-2- (3,5-difluoro-4-chlorophenyl) -6- [2- (4-heptylphenyl) ethyl] naphthalene 1-fluoro-2-(4-trifluorofluorenyloxyphenyl) ) -6- [2- (4-Ethylphenyl) ethyl] naphthalene 1-town-2-(4-tri-Itmethoxyphenyl) -6-[2- (4-propylphenyl) ethyl] Naphthalene 1-fluoro-2- (4-trifluoromethoxyphenyl) -6- [2- (4-butylphenyl) ethyl] naphthalene 1-H-2- (4-trifluoromethoxyphenyl) -6- [2- (4-pentylphenyl) ethyl] naphthalene 1-fluoro-2- (4-trimethoxymethoxyphenyl) -6- [2- (4-hexylphenyl) ethyl] naphthalene 1-Gas-2-(4-trigasmethoxymethoxyphenyl) -6-[2- (4-heptylphenyl) ethyl] naphthalene 1-IL-2- (3-fluoro-4 -trifluoromethoxy Phenyl) -6_ [2- (4-ethylphenyl) ethyl] naphthalene 1-gas-2- (3-gas-4-trifluoromethoxyphenyl) -6- [2- (4-propylbenzene (Yl) ethyl] naphthalene 1-fluoro-2- (3-fluoro ^ 4-trifluoroalkoxyphenyl) -6- [2- (4-butphenyl) ethyl] naphthalene 1-fluoro-2- ( 3-fluoro-4-trifluorofluorenyloxyphenyl) -6- [2- (4-pentylphenyl) ethyl] naphthalene 1-benz-2- (3-benzyl-4-trifluorofluorenylphenyl) -6- [2- (4-hexylphenyl) ethyl] naphthalene 1-fluoro-2- (3- -4-trifluorofluorenoxyphenyl) -6- [2- (4- Heptyl) ethyl] naphthalene 1-fluoro ^ 2- (3,5-bis-4 -trifluorofluorenoxyphenyl) -6- [2- (4-ethylphenyl)

Page 124 528794 V. Description of the invention (122) Ethyl] naphthalene 1-fluoro-2- (3,5-difluoro-4 -triIImethoxyphenyl) -6-[2-(4-propylphenyl) ) Ethyl] naphthalene 1-fluoro-2- (3,5 -digas-4 -trifluoromethoxyphenyl) -6- [2- (4-butylphenyl) ethyl] naphthalene 1-benz-2 -(3,5-diIL-4 -trifluorofluorenoxyphenyl) -6-[2- (4-pentylphenyl) ethyl] naphthalene 1-mer-2- (3,5-difluoro-4 -Trifluoromethoxyphenyl) -6- [2- (4-hexylphenyl) ethyl] naphthalene

1- It-2- (3,5-difluoro-4 -trifluorofluorenoxyphenyl) -6- [2- (4-heptylphenyl) ethyl] naphthalene

1-fluoro-2- (4-difluoromethoxyphenyl) -6- [2- (4-ethylphenyl) ethyl] naphthalene 1-fluoro-2- (4-difluoromethoxyphenyl)- 6- [2- (4-propylphenyl) ethyl] naphthalene 1-fluoro-2- (4-diILoxophenyl) -6- [2- (4-butylphenyl) ethyl] naphthalene 1 -Fluoro-2- (4-difluoromethoxyphenyl) -6-[2- (4-pentylphenyl) ethyl] naphthalene 1-fluoro-2- (4-diILoxophenyl) -6 -[2- (4-hexylphenyl) ethyl] naphthalene1-dun-2- (4-diILoxophenyl) -6- [2- (4-heptylphenyl) ethyl] naphthalene 1- Fluoro-2-(3-fluoro-4 -difluoromethoxyphenyl) -6- [2- (4-ethylphenyl) ethyl] naphthalene 1-fluoro-2- (3-IL-4 -divinyl Methoxyphenyl) -6- [2- (4-propylphenyl) ethyl] naphthalene 1-fluoro-2-(3-fluoro-4-digasmethoxymethoxyphenyl) -6- [2-(4 -Butylphenyl) ethyl] naphthalene 1-fluoren-2- (3-fluoro-4 -difluoroifluorenyloxy) -6- [2- (4-pentylphenyl) ethyl

Page 125 528794 V. Description of the invention (123) yl] naphthalene 1-gas-2- (3-fluoro-4-difluoromethoxyphenyl) -6- [2- (4-hexylphenyl) ethyl] Naphthalene 1-fluoro-2- (3-IL-4 4-dioxanyloxyphenyl) -6- [2- (4-heptylphenyl) ethyl] naphthalene 1-fluoro-2-(3,5-di Fluoro-4 -difluorofluorenoxyphenyl) -6- [2- (4-ethylphenyl) ethyl] naphthalene 1-fluoro-2-(3,5-difluoro ^ 4-difluoromethoxyphenyl )-6-[2- (4-propylphenyl) ethyl] qin

1-Lan-2- (3,5-diIL-4 -difluoromethoxyphenyl) -6- [2- (4-butylphenyl) ethyl] naphthalene 1-Jan-2- (3,5 -Difluoro-4 -difluorofluorenoxyphenyl) -6- [2- (4-pentylphenyl) ethyl] naphthalene 1-fluoro1-2- (3,5-difluoro-4-difluoromethyl) Oxyphenyl) -6- [2- (4-hexylphenyl) ethyl] naphthalene 1-fluoro-2-(3,5-diphenyl-4-difluoro ^ pyroxyphenyl) -6- [2 -(4-heptylphenyl) ethyl] qin 1-fluoro-2- (4-trifluorotolyl) -6- [2- (4-ethylphenyl) ethyl] naphthalene

1-fluoro-2- (4-trifluorotolyl) -6- [2- (4-propylphenyl) ethyl] naphthalene 1-It-2- (4-trifluorofluorenyl) -6-[ 2- (4-Butylphenyl) ethyl] naphthalene 1-11-2- (4-trifluorotolyl) -6-[2- (4-pentylphenyl) ethyl] naphthalene 1-fluoro-2- (4-trifluorotolyl 6- [2- (4-hexylphenyl) ethyl] naphthalene 1-fluoro-2- (4-trifluorotolyl) -6- [2- (4-heptylphenyl) Ethyl] naphthalene 1-fluoro-2- (3-fluoro-4 -trifluoroi-tolyl) -6- [2- (4-ethylphenyl) ethyl]

Page 126 528794 V. Description of the invention (124) Naphthalene 1-gas-2- (3-fluoro-4-tri IL tolyl) -6- [2- (4-propylphenyl) ethyl] Naphthalene 1-II -2- (3-fluoro-4 -tri-IL fluorenyl) -6- [2- (4-butylphenyl) ethyl] naphthalene 1-gas-2- (3-fluoro-4-trigas benzene ) -6- [2- (4-pentylphenyl) ethyl] naphthalene 1-fluoro-2- (3-fluoro-4-trifluorotolyl) -6- [2- (4-hexylphenyl) (Ethyl) naphthalene

1-fluoro ^ -2- (3-Ail-4-triILtolyl) -6- [2- (4-heptylphenyl) ethyl] naphthalene 1-fluoro-2- (3,5_difluoro- Trifluoro i tolyl) -6- [2- (4-ethylphenyl) ethyl] qin 1-fluoro-2- (3,5-digas-4 -trifluoro i-phenyl) -6- [ 2- (4-propphenyl) ethyl] naphthalene 1-gas-2- (3,5-difluoro4-trifluorofluorenylphenyl) -6- [2- (4-butylphenyl) ethyl] Naphthalene

1-Gas-2- (3,5-digas-4-trifluoro ^ phenyl) -6- [2- (4-pentylphenyl) ethyl] naphthalene 1-benz-2- (3,5 -Digas-4 -trifluoroi-phenyl) -6- [2- (4-hexylphenyl) ethyl] naphthalene 1-fluoro ^ 2- (3,5-digas-4 -triIL tolyl ) -6- [2- (4-heptylphenyl) ethyl] naphthalene 1-fluoro-2- (4-methoxyphenyl) -6-[2- (4-ethylphenyl) ethyl] naphthalene

Page 127 528794 V. Description of the invention (125) 1-fluoro-2- (4-fluorenoxyphenyl) -6- [2- (4-propylphenyl) ethyl] naphthalene 1- | t-2- ( 4-methoxyphenyl) -6-[2- (4-butylphenyl) ethyl] naphthalene 1-fluoro-2- (4-fluorenylphenyl) -6- [2- (4-pentylphenyl ) Ethyl] naphthalene 1-fluoro-2- (4-fluorenyloxy) -6- [2- (4-hexylphenyl) ethyl] naphthalene 1-fluoro-2- (4-fluorenylphenyl) -6- [2- (4-heptylphenyl) ethyl] naphthalene 1-fluoro-2- (3-fluoro-4-fluorenoxyphenyl) -6- [2- (4-ethylphenyl) ethyl ] Naphthalene 1-fluoro-2- (3-fluoro-4-methoxyphenyl) -6- [2- (4-propylphenyl) ethyl] naphthalene 1-It-2- (3-fluoro-4- Methoxyphenyl) -6- [2- (4-butylphenyl) ethyl] naphthalene 1-fluoro-2- (3-fluoro-4-methoxyphenyl) -6- [2- (4-pentyl Phenyl) ethyl] naphthalene 1-fluoro-2- (3-fluoro-4-methoxyphenyl) -6- [2- (4-hexyl) ethyl] naphthalene 1-fluoro-2- (3 -Fluoro-4-fluorenoxyphenyl) -6- [2- (4-heptylphenyl) ethyl] naphthalene 1-fluoro-2-(3,5-difluoro-4-methoxyphenyl) -6 -[2- (4-Ethylphenyl) ethyl] naphthalene 1-fluoro-2- (3,5-difluoro-4-oxophenyl) -6- [2- (4-propylphenyl) ethyl Yl] naphthalene 1-fluoro-2- (3,5-difluoro-4-methoxyphenyl) -6- [2- (4-butylphenyl) ethyl] naphthalene 1-gas-2- (3, 5 -di 4-methoxyphenyl ) -6-[2- (4-pentylphenyl) ethyl] naphthalene 1-fluoro-2- (3, 5-difluoro-4-methoxyphenyl) -6- [2- (4-hexylbenzene ) Ethyl] naphthalene 1-fluoro-2- (3,5-difluoro-4-fluorenyloxy) -6- [2- (4-heptylphenyl) ethyl] naphthalene 1-town-2- (4-Dilute propoxyphenyl) -6- [2- (4-ethylphenyl) ethyl] naphthalene

Page 128 528794 V. Description of the invention (126) Oxyphenyl) + [2- (4-propphenyl) ethyl] I ran-2- (4-allyl phenyl) _6_ [2_ (4_ butylbenzene) Group) ethyl cap 1-fluoro-2- (4-allyloxyphenyl) _6_ [2_ (4-pentylphenyl) ethyl j 1-fluoro-2- (4-allyloxyphenyl) _6_ [ 2_ (4_hexylphenyl) ethyl cover 1-,-2- (4-allyloxyphenyl) _6_ [2_ (4_heptylphenyl) ethyl tomb 1-ran-2- (4-. 曱Phenyl) _6_ [2_ (4_ethylphenyl) ethyl] naphthalene "1-fluoro-2- (4-methylbenzyl) _6_ [2_ (4_propylphenyl) ethyl] naphthalene 1-fluoro-2 -(4-fluorenyl) _6_ [2_ (4-butylphenyl) ethyl] naphthalene, 2- (4-fluorenyl) _6_ [2_ (4-pentylphenyl) ethyl] naphthalene 1-fluoro -2- (4-methylbenzyl) _6_ [2_ (4-hexylphenyl) ethyl] naphthalene 1-fluoro-2- (4-tolyl) _6_ [2_ (4_heptylphenyl) ethyl] naphthalene 1-fluoro-2- [4- (3-butenyl) phenyl] _6_ [2_ (4_ethylphenyl) ethoxy 1-fluoro-2- [4- (3-butenyl) phenyl] _6_ [2_ (4_Propylphenyl) ethanedifluoro-2- [4- (3-butenyl) phenyl] _6_ [2_ (4_butylphenyl) ethyl ^ = Buran-2- [4 -(3-butenyl) phenyl] _6_ [2_ (4-pentylphenyl) ethenyl 1-fluoro-2- [4- (3-butenyl) phenyl] _6_ [2 — (4_ Hexylphenyl) ethyl ^ fluoro-2- [4- (3-butenyl) Base] _6_ [2_ (4_heptylphenyl) ethoxy pen [Example 7] Bu defeat-2- (3,4,5_trisylphenyl) -6_ (4_propylbenzene "Qin Zhishen J ^ 6 -(4-Propylphenyl) -2-naphthol is synthesized by 50 g of 6-bromo-2-naphthol and 48 g of 4-propenylboronic acid (this compound is made of 4-propyl bromide) Sub-reagent, reacted with trimethyl borate, and then hydrolyzed with hydrochloric acid to synthesize it) dissolved in toluene 2 0 ^ and 100 ml of ethanol, and added 200 ml of potassium carbonate aqueous solution

Page 129 528794 V. Description of the invention (127), and then add 2. 6 g of tris (triphenylphosphine) palladium (0) and heat to reflux for 6 hours. After cooling to room temperature, the organic layer was separated, and the aqueous layer was extracted with toluene. The organic layers were combined, washed successively with dilute hydrochloric acid, water, and saturated saline, and dried over anhydrous sodium sulfate. The solvent was distilled off to obtain 47 g of 6- (4-propyl) phenyl-2-naphthol crystals. Thus, white crystals of buflo-2- (3-4, 5-trifluorophenyl) -6- (4-propylphenyl) naphthalene were obtained in the same manner as (5-d) and (5-e). . The following compounds can also be obtained.

1-fluoro-2- (3,4-diILphenyl) -6- (4-ethylphenyl) naphthalene 1-fluoro-2- (3,4-diphenylphenyl) -6- (4-propane Phenyl) naphthalene 1-fluoro-2- (3, 4-difluorophenyl) -6- (4-butylphenyl) naphthalene 1-fluoro-2- (3,4-difluorophenyl) -6- (4-pentylphenyl) naphthalene 1-fluoro-2- (3,4,5-trifluorophenyl) -6- (4-ethylphenyl) naphthalene 1-fluoro-2- (3,4,5- Trifluorophenyl) -6- (4-propylphenyl) naphthalene1-fluoro-2- (3,4,5-trifluorophenyl) -6- (4-butylphenyl) naphthalene 1-IL-2 -(3,4,5-trisylphenyl) -6- (4-pentylphenyl) naphthalene 1-fluoro-2- (4-fluorophenyl) -6- (4-ethylphenyl) naphthalene 1- For 2- (4-fluorophenyl) -6- (4-propylphenyl) naphthalene 1-It-2- (4-fluorophenyl) -6- (4-butylphenyl) naphthalene 1-fluoro- 2- (4-fluorophenyl) -6- (4-pentylphenyl) naphthalene1-fluoro-2- (4-fluorophenyl) -6- (4-hexylphenyl) naphthalene 1-fluoro-2- (4-fluorophenyl) -6- (4-heptylphenyl) naphthalene1-IL-2- (4-fluorophenyl) -6- [4- (3-butenyl) phenyl] naphthalene 1- 2- (3-Dentylphenyl) -6- (4-ethylphenyl) naphthalene

Page 130 528794 V. Description of the invention (128) 1-fluoro-2- (3-phenylphenyl) -6- (4-propylphenyl) naphthalene 1-fluoro-2- (3-fluorophenyl) -6 -(4-Butylphenyl) naphthalene 1-fluoro-2- (3-Itphenyl) -6- (4-pentylphenyl) naphthalene 1-fluoro-2- (3-phenylphenyl) -6- ( 4-hexylphenyl) naphthalene 1-fluoro-2- (3-fluorophenyl) -6- (4-heptylphenyl) naphthalene 1-gas-2- (3-fluorophenyl) -6- [4- (3-Butylfluorenyl) phenyl] naphthalene 1-den-2- (3,5-difluorophenyl) -6- (4-ethylphenyl) naphthalene 1-fluoro-2- (3,5-difluorobenzene ) -6- (4-propylphenyl) naphthalene 1-fluoro-2- (3,5-difluorophenyl) -6- (4-butylphenyl) naphthalene

1-fluoro-2- (3,5-diILphenyl) -6- (4-pentylphenyl) naphthalene1-dun-2- (3,5-diphenylphenyl) -6- (4-hexane Phenyl) naphthalene 1-fluoro-2- (3,5-didunphenyl) -6- (4-heptylphenyl) naphthalene 1-fluoro-2- (3,5-difluorophenyl) -6- [4- (3-butenyl) phenyl] naphthalene 1-fluoro-2 -phenyl-6- (4-ethylphenyl) naphthalene 1-fluoro-2 -phenyl-6- (4-propylphenyl) Naphthalene 1-gas-2 -phenyl-6- (4-butylphenyl) naphthalene 1-gas-2 -phenyl-6- (4-pentylphenyl) Cai 1-fluoro-2 -phenyl-6- (4-Hexylphenyl) naphthalene

1-Dun-2 -phenyl-6- (4-heptylphenyl) naphthalene 1-benzyl-6- [4- (3-butenyl) phenyl] naphthalene 1-fluoro-2- (4- Chlorophenyl) -6_ (4-ethylphenyl) naphthalene1-fluoro-2- (4-chlorophenyl) -6- (4-propylphenyl) naphthalene 1-fluoro-2- (4-chlorophenyl ) -6- (4-butylphenyl) naphthalene 1-fluoro-2- (4-chlorophenyl) -6- (4-pentylphenyl) naphthalene

Page 131 528794 V. Description of the invention (129) 1-fluoro-2- (4-chlorophenyl) -6- (4-hexylphenyl) naphthalene 1-fluoro-2- (4-chlorophenyl) -6 -(4-heptylphenyl) naphthalene 1-fluoro-2- (4-chlorophenyl) -6- [4- (3-butenyl) phenyl] naphthalene 1-benz-2- (3-gas- 4-chlorophenyl) -6- (4-ethylphenyl) naphthalene1-benz-2- (3-gas-4-chlorophenyl) -6- (4-propylphenyl) naphthalene 1-fluoro-2 -(3- IL-4-chlorophenyl) -6- (4-butylphenyl) naphthalene 1-fluoro-2- (3-decan-4-chlorophenyl) -6- (4-pentylphenyl) Naphthalene 1-fluoro-2- (3-fluoro-4-chlorophenyl) -6- (4-hexylphenyl) naphthalene 1-fluoro-2- (3-fluoro-4-chlorophenyl) -6- ( 4-heptylphenyl) naphthalene 1-fluoro-2- (3-fluoro-4-chlorophenyl) -6- [4- (3-butenyl) phenyl] naphthalene 1-fluoro-2- (3, 5-difluoro-4-chlorophenyl) -6- (4-ethylphenyl) naphthalene1-fluoro-2- (3,5-difluoro-4-chlorophenyl) -6- (4-propenebenzene ) Naphthalene 1-fluoro-2- (3,5-difluoro-4-chlorophenyl) -6- (4-butylene) naphthalene 1-fluoro-2- (3,5-digas-4- Chlorophenyl) -6- (4-pentylphenyl) naphthalene1-benz-2- (3,5-difluoro-4-chlorophenyl) _6- (4-hexylphenyl) naphthalene 1-fluoro-2 -(3,5-difluoro-4-Gaphenyl) -6- (4-heptylphenyl) naphthalene 1-Ga-2- (3,5-di4-chlorophenyl) -6- [4- ( 3-butenyl) phenyl] naphthalene 1-fluoro-2- (4 -Trifluoromethoxyphenyl) -6- (4-ethylphenyl) naphthalene1-fluoro-2- (4-trifluorofluorenoxyphenyl) -6- (4-propylphenyl) naphthalene 1-fluoro- 2- (4-trifluoromethoxyphenyl) -6- (4-butylphenyl) naphthalene 1-IL-2- (4-trifluoromethoxyphenyl) -6- (4-pentylphenyl) naphthalene 1-Gas-2- (4-trifluoroimethoxyphenyl) -6- (4-hexylphenyl) naphthalene 1-fluoro-2- (4-tri-Itoxophenyl) -6- (4- Heptyl) Qin

Page 132 528794 V. Description of the invention (130) 1-fluoro-2-(4-trifluoromethoxyphenyl) -6- [4- (3-butenyl) phenyl] naphthalene 1-fluoro-2- (3-fluoro-4 -trifluoromethoxyphenyl) -6- (4-ethylphenyl) naphthalene 1-fluoro-2- (3-fluoro-4 -trifluoroαmethoxyphenyl) -6- ( 4-propylphenyl) naphthalene 1-fluoro-2- (3-fluoro-4-trifluorofluorenyloxyphenyl) -6- (4-butylene) naphthalene 1-fluoro-2- (3-fluoro-4 -Trifluoromethoxyphenyl) -6- (4-pentylphenyl) naphthalene 1-fluoro-2-(3-fluoro-4 -tri-Itoxophenyl) -6- (4-hexylphenyl) naphthalene 1-Gas-2-(3-fluoro-4_trifluoromethoxyphenyl)-6- (4-heptylphenyl) naphthalene 1-fluoro-2- (3- 4 -trifluoromethoxyphenyl)- 6- [4- (3-Butanediyl) phenyl] naphthalene 1-gas-2- (3,5-difluoro-4-trifluorofluorenoxyphenyl) -6- (4-ethylphenyl) naphthalene 1-Gas-2- (3,5-difluoro-4 -trifluoro1methoxyphenyl) -6- (4-propylphenyl) naphthalene 1-fluoro-2- (3,5-difluoro-4 -Trifluorofluorenylphenyl) -6- (4-butylphenyl) naphthalene 1-fluoro-2- (3,5-difluoro-4 -trifluorophosphonyl) -6- (4-pentylbenzene ) Naphthalene 1-fluoro-2- (3,5-ditrifluorofluorenoxyphenyl) -6- (4-hexylphenyl) naphthalene 1-fluoro-2- (3,5-difluoro-4 -tri Phenyloxyphenyl) -6- (4-heptylphenyl) naphthalene 1-fluoro -2- (3,5 -difluoro-4 -tridecylmethoxyphenyl) -6- [4- (3 -butylfluorenyl) phenyl] naphthalene 1-fluoro-2- (4-difluoromethoxy Phenyl) -6- (4-ethylphenyl) naphthalene 1-fluoro-2-(4-difluoromethoxyphenyl) -6- (4-propylphenyl) naphthyl-2- (4-di Fluoromethoxyphenyl) -6- (4-butylphenyl) naphthalene 1-fluoro ^ 2- (4-difluoromethoxyphenyl) -6- (4-pentylphenyl) qin 1-fluoro-2- (4-Dimethoxymethoxyphenyl) -6- (4-hexylphenyl) qin 1-fluoro-2- (4-difluoromethoxyphenyl) -6- (4-heptylphenyl) naphthalene 1- Fluoro-2-(4-difluoroi-methoxyphenyl) -6- [4- (3-butylfluorenyl) phenyl] naphthalene

Page 133 528794 V. Description of the invention (131) 1-fluoro-2- (3-fluoro-4-difluorofluorenyloxyphenyl) -6-(4-ethylphenyl) naphthalene 1-gas-2-(3 -Fluoro-4 -diIL methoxyphenyl) -6- (4-propylphenyl) naphthalene 1-say-2- (3-fluoro-4-digasmethoxymethoxyphenyl) -6-(4-butane Phenyl) naphthalene 1-fluoro-2- (3- | 1-4-difluorofluorenoxyphenyl) -6- (4-pentylphenyl) naphthalene 1--2-(3-fluoro-4-difluoro Phenoxyphenyl) -6- (4-hexylphenyl) naphthalene1-fluoro-2- (3-fluoro-4 -difluorofluorenyloxyphenyl) -6- (4-heptylphenyl) naphthalene 1-oxyl -2- (3-fluoro ^ 4-difluorofluorenyloxyphenyl) -6-[4-(3-butanyl) phenyl] naphthalene 1-fluoro-2-(3,5-difluoro-4- Difluoromethoxyphenyl) -6- (4-ethylphenyl) naphthalene1-benzyl-2- (3,5-difluoro-4-difluorofluorenyloxyphenyl) -6- (4-propylphenyl ) Naphthalene 1-fluoro-2- (3,5-digas-4_digasmethoxyphenyl) -6- (4-butylphenyl) naphthalene 1-fluoro ^ 2-(3,5-difluoro- 4-difluoromethoxyphenyl) -6- (4-pentylphenyl) naphthalene 1-fluoro-2- (3,5 -difluoro-4 -difluoro "oxophenyl) -6-(4- Hexylphenyl) naphthalene 1-fluoro-2- (3,5-difluoro-4-difluoromethoxyphenyl) -6- (4-heptylphenyl) naphthalene 1-fluoro-2- (3,5- Digas-4 -difluoroi methoxyphenyl) -6-[4- ( 3-butylfluorenyl) phenyl] benzene 1-gas-2- (4-trifluorotolyl) -6- (4-ethylphenyl) naphthyl-2- (4-trifluorotolyl) -6 -(4-Propylphenyl) naphthalene 1-to-2- (4-trifluorotolyl) -6- (4-butylphenyl) naphthalene 1-to-2- (4-triphenyltolyl) -6 -(4-pentylphenyl) naphthyl-2- (4-trifluorofluorenyl) -6- (4-hexylphenyl) naphthalene 1-fluoro-2-(4-trifluorotolyl) -6 -(4-heptylphenyl) naphthalene 1-fluoro-2- (4-trifluorofluorenylphenyl) -6- [4- (3-butenyl) phenyl] naphthalene 1-fluoro-2- (3- Fluoro-4_trifluorotolyl) -6- (4-ethylphenyl) naphthalene

Page 134 528794 V. Description of the invention (132) 1-Dun-2- (3-fluoro-4 -trifluoroα-tolyl) -6- (4-propylphenyl) naphthalene 1-IL-2- (3- Fluoro-4-trifluorotolyl) -6- (4-butylphenyl) naphthalene 1-fluoro-2- (3-fluoro-4-trifluorotolyl) -6- (4-pentylphenyl) naphthalene 1 -Fluoro-2- (3-H-4-trifluorotolyl) -6- (4-hexylphenyl) naphthalene 1-fluoro-2- (3-deca-4-trifluorotolyl) -6-( 4-heptylphenyl) naphthalene 1-gas-2-(3-dun-4-trifluorofluorenylphenyl) -6- [4- (3-butenyl) phenyl] naphthalene 1-fluoro-2-( 3,5-Digas-4 -trifluorotolyl) -6-(4-ethylphenyl) naphthalene 1-gas-2- (3,5-difluoro ^ 4-trifluorofluorenylphenyl 6- (4 -Propylphenyl) naphthalene 1-fluoro-2- (3,5-difluoro-4 -trifluorotolyl) -6- (4-butylphenyl) naphthalene 1-speak-2- (3,5-di IL-4 -trifluorotolyl) -6- (4-pentylphenyl) naphthalene 1-fluoro-2- (3,5-difluoro-4 -trifluorotolyl) -6- (4-hexylphenyl ) Naphthalene 1-fluoro-2- (3,5-difluoro-4-trifluorotolyl) -6- (4-heptylphenyl) naphthalene 1-say-2- (3,5-diH-4- Trifluorotolyl) -6-[4- (3-butlyl) phenyl] naphthalene 1-fluoro-2- (4-fluorenylphenyl) -64-ethylphenyl) naphthalene 1-fluoro-2- (4-methoxyphenyl) -6- (4-propylphenyl ) Naphthalene 1-fluoro-2- (4-methoxyphenyl) -6- (4-butylphenyl) naphthalene 1-fluoro-2- (4-fluorenylphenyl) -6- (4-pentylphenyl ) Naphthalene 1-fluoro-2- (4-methoxyphenyl) -6- (4-hexylphenyl) naphthalene 1-fluoro-2- (4-fluorenylphenyl) -6- (4-heptylphenyl) ) Naphthalene 1-fluoro-2- (4-fluorenyloxy) -6- [4- (3-butenyl) phenyl] naphthalene 1-fluoro-2- (3-fluoro-4-methoxyphenyl ) -6- (4-ethylphenyl) naphthalene 1-fluoro-2- (3-It-4-fluorenylphenyl) -6- (4-propylphenyl) naphthalene

Page 135 528794 V. Description of the invention (134) 1 Fluoro 2 (4-Tolyl) -6- (4-Hexyl 1-fluoro-2- (4-tolyl) -6_ (4_heptyl) -Lan-2- (4 ~ fluorenyl) -6- [4-a (3-monobutene ^ bufluoro-2- [4- (3-butenyl) benzyl] -terbinaphthalene 1-gas- 2- [4- (3-τ dilute) phenyl] + (4_ ^ di ^ Pl _2 — [4 — (3 ~ butenyl) phenyl] -6- (4-butadiene) ^ 1-fluoro-2- [4- (3-butenyl) benzene] _6-di ^ 1-gas-2-UQ-butenyl) phenyl] _6 — mH 1-fluorene-2- [4- (3 -Butenyl) phenyl] -6_ (diphenylm [4- (3-butanyl) phenyl] -6_ [[Example 8] Fluoro H fw ^ Woyl) naphthyl) naphthalene) naphthalene: Trans 4-vinylcyclohexyl In Example 5, except for the use of cyclohexyl-4, 4, dibenzyl X in place of 4-propanecyclohexanone, the Grignard reaction was also performed = potassium gas instead of p-toluene After dehydration of the (reaction product) with sulfonic acid, ethylene glycol was added to the acid solution, while azeotropic water was excluded from the system, and heated to reflux under cooling. Cool to room temperature, water, saturated sodium bicarbonate aqueous solution ,: Add saline and wash sequentially, dehydrate and dry with anhydrous sodium sulfate, distill off the solvent and obtain 4- (6-methyl Oxynaphthalene-2 -yl) -3 -cyclohexene acetal. To dissolve it, and after performing contact reduction in the same manner as (2-b), add formic acid and stir; stir. After cooling, add water, After the separated toluene layer was washed, the solvent was removed. The obtained crude crystals were recrystallized by ethanol to obtain 4- (6 ~ methoxymethoxy-2-yl) cyclohexanone crystals. Mixed solvent soluble in toluene and THF ^

Page 137 528794 V. Description of the invention (133)

1-fluoro-2- (3-H-4-methoxyphenyl) -6- (4-butylphenyl) naphthalene 1-fluoro-2-(3-fluoro-4-methoxyphenyl) -6- (4-pentylphenyl) naphthalene 1-fluoro-2- (3-fluoro-4-methoxyphenyl) -6- (4-hexylphenyl) naphthalene 1-fluoro-2- (3-fluoro-4- Methoxyphenyl) -6- (4-heptylphenyl) naphthalene 1-fluoro-2- (3-IL-4-fluorenyloxyphenyl) -6-[4- (3-butanyl) phenyl] Naphthalene 1-deca-2- (3,5-digas-4-methoxyphenyl) -6- (4-ethylphenyl) naphthalene 1-fluoro-2- (3,5-diIt-4-methyl Oxyphenyl)-6- (4-propylphenyl) naphthalene 1-fluoro-2- (3,5-difluoro-4-methoxyphenyl) -6- (4-butylphenyl) naphthalene 1-fluoro -2- (3,5-difluoro-4-fluorenylphenyl) -6- (4-pentylphenyl) naphthalene 1-fluoro-2- (3,5-difluoro-4-methoxyphenyl) -6- (4-hexylphenyl) naphthalene 1-fluoro-2- (3,5-difluoro-4-fluorenoxyphenyl) -6- (4-heptylphenyl) naphthalene 1-fluoro-2-( 3,5-difluoro-4-methoxyphenyl) -6- [4- (3-butenyl) phenyl] naphthalene 1-fluoro-2- (4-dilute propoxyphenyl) -6- ( 4-Ethylphenyl) naphthalene1-methyl-2- (4-dilute propoxyphenyl) -6- (4-propylphenyl) naphthalene 1-methyl-2- (4-dilute propoxyphenyl) -6 -(4-Butylphenyl) naphthalene 1-fluoro-2- (4-allyloxyphenyl) -6- (4-pentylphenyl) naphthalene 1-fluoro-2- (4-dilute propoxy Yl) -6- (4_ hexyl) naphthalene

1-dun-2- (4-dipropoxyphenyl) -6- (4-heptylphenyl) naphthalene 1-dun-2- (4-allyloxyphenyl) -6- [4- (3- Butenyl) phenyl] naphthalene1-naphthyl-2- (4-tolyl) -6 ™ (4-ethylphenyl) naphthalene1-fluoro-24-fluorenylphenyl) -6- (4-propylphenyl ) Naphthalene 1-fluoro-2-(4-fluorenylphenyl) -6- (4-butylphenyl) naphthalene 1--fluorenyl) -6-(4-pentylphenyl) naphthalene

Page 136 528794-丨 V. Description of the invention (135) Cooling, to which reagents consisting of evolved methoxymethyltriphenylscale and the third potassium butoxide 2 are added. Restore the room temperature, add water and sinter, and add the following layers: No: After washing, wash with water / methanol mixed solvent, add dilute hydrochloric acid, and heat to reflux for 1 hour; here; = solvent and get the reverse 4- (6-Methoxynaphthyl is dried and dissolved in THF, and then added with a moth-formed human body. It is made to be a reagent. Restore the room temperature, add ~ a second potassium butoxide After the solution is dissolved, the solvent is mixed with water / methanol, and the solvent is removed from the layer without using solvent. Shixi Chromatographic Chromatography \ Medium :: Washing. After dehydration and drying, Gu ethylene cyclohexyl H-methoxy Purified to obtain 2- (trans 4- and as) was performed in the same way, and the title was obtained by ^, / (M, (5-d), group) -6- (trans 4-vinylcyclohexyl) naphthalene. Rat 2 ~ (3,4-difluorobenzene can also obtain the following compounds. 1 monofluoro-2- (3,4,5 ~ tri-n-poor 1-fluoro-2- (4-fluorobenzyl) _6 ~ (E ^^ (J4 '= cyclohexyl) naphthalene 1-fluoro-2- (3-fluorobenzyl) _6 vinylhexyl) naphthalene 1-fluoro-2- (3,5-difluorophenyl) = ene ring Hexyl) naphthalene 1-fluoro-2-phenyl-6 ~ (trans p ^ trans 4 ~ vinylcyclohexyl) benzylfluoro-2rchlorobenzyl) di = Qin 1-fluoro_2- (3- 1-4— Chlorobenzyl) acetamidine Hexyl) naphthalene 1-fluoro_2- (3 '5-difluoro-1 4-chlorobenzyl) (_di = diluted cyclohexyl) Qin ~ vinylcyclohexyl) naphthalene Page 138 528794 5. Description of the invention (136 ) 1-Fluoro-2- (4-trifluoromethoxyphenyl) -6- (trans 4-ethenylcyclohexyl) naphthalene 1-fluoro-2- (3-fluoro-4-trifluoroα 曱 oxophenyl )-6- (trans 4-Ethylcyclohexyl) naphthalene 1-fluoro-2- (3,5-ditrifluoromethoxyphenyl) -6-(trans 4-vinylcyclohexyl) naphthalene 1-fluoro-2 -(4-Dimethoxymethoxyphenyl) -6- (trans 4-ethoxycyclohexyl) naphthalene 1-fluoro-2-(3-fluoro-4 -difluoromethoxyphenyl) -6- (trans-4 -Ethylcyclohexyl) naphthalene

1-fluoro-2- (3,5 -difluoro-4 -difluoro 1-oxophenyl) -6- (trans 4-ethylenecyclohexyl) naphthalene 1-gas-2-(4-trifluorotolyl) ) -6-(trans 4-Ethylcyclohexyl) naphthalene 1-gas-2-(3-fluoro-4-trigastolyl) -6- (trans 4-Ethylcyclohexyl) naphthalene 1-benz-2 -(3,5-difluoro-4-trifluorotolyl) -6- (trans 4-ethenylcyclohexyl) naphthalene 1-fluoro 2- (4-fluorenylphenyl) -6-(trans 4-ethyl Diluted cyclohexyl) naphthalene 1-fluoro ^ 2- (3-fluoro-4-methoxyphenyl) -6- (trans 4-ethenylcyclohexyl) naphthalene 1 4-monomethoxyphenyl) 6- (trans 4-ethylenecyclohexyl) naphthalene

1-Lan-2-(4-Dipropoxyphenyl) -6- (trans 4-ethylenecyclohexyl) naphthalene 1-fluoro-24-fluorenylphenyl) -6- (trans 4-vinylcyclohexyl) naphthalene 1-Fluoro-2- [4- (3-butenyl) phenyl] -6- (trans 4-ethenylcyclohexyl) naphthalene [Example 9] 1-fluoro-2- (4-cyanophenyl) Synthesis of 6- (trans 4-propanecyclohexyl) naphthalene enables 1-fluoro-2- (4,4-difluorenyl-1,3-oxazolidin-2-yl) phenyl-6- (trans

Page 139 528794 V. Description of the invention (137) 4-propanyl · hexyl) Qin (this one's humanized phenyl) -4, 4-difluorenyl 1 3 dimer / di in (5: f) Except for the use of 2- (4- desert for I 5, the same results were obtained using j and 1π 疋 instead of 3,4 — under the gas y-bromobenzene. 'After the temperature of 25 ° C, remove the excess under reduced pressure ^: Stir for 5 hours at 11 ° C to extract the aqueous layer. Combined with: phosphorus dioxide. To this add dilute hydrochloric acid' borrow And saturated saline solution. Twenty-two liters of water and saturated sodium bicarbonate were used to dissolve the water. The solvent was distilled off, and the coagulant 1 was used to dehydrate the dry alcohol and recrystallize it by using anhydrous sodium sulfate to obtain the title. Hexane) was purified, and then the same compound I. 4g was obtained by using B. Fluoro-2- (4-cyanophenyl), 6- (trans-i-fluoro-2- (4-cyanophenyl) + (trans 4-butane: [= 1-fluoro-2- (4-cyanophenyl longhexyl) naphthalene ...- cyanophenylphosphonium ((; ==)); 2- 1-2- (4-cyanophenyl) ~ 6 — (trans 4 _ '[[Example 10] Buflu-2 ~ (3_fluoro_4_ ^ hexyl) qin) naphthalene synthesis lice 4 mouse benzyl) -6_ (trans 4-propanecyclohexyl lutein benzene Synthesis of 6- (trans4-propane (10-a) buflo-2— (3 ~ fluoro-4—trifluoroτhexyl) naphthalene) 20 g of 1-fluoro-2- (3 ~ fluoro— 4-This compound is used in (5-f) in addition to butan-6- (trans-4-propanehexyl) naphthalene instead of 3,4-difluoro-1-bromobenzene. Br-3-fluoro-4-methoxybenzene is 3-said-4-methoxyphenyl) -6- (trans 4-propane ring, sample J, and ^ (obtained by removing the methyl group) ), Xuan Yu— &gt; Tu) Qin 'secondly borrowed hydrobromic acid to 80ml of methane in one gas, and secondly, to this 528794 V. Description of the invention (138) Add difluoromethane anhydride 1 5 · 8 g under ice cold For this reason, be careful to drop the roar and bite 10 m 1 'so that the liquid temperature does not exceed 5 C. At the end of the dropwise addition, also teach at this temperature for 1 hour. Add 20 ml of water to stop the reaction, and then wash the organic with 20 ml of water After the second layer, it was dehydrated and dried by anhydrous sodium sulphate, and then the solvent was removed under reduced pressure, and purified by silica gel chromatography (hexane) to obtain 丨 —fluoro-2— (3y ^^-trifluoromethyl). Luteinic acid phenyl) -6- (trans4-propanecyclohexyl) naphthalene 24.3g. (10-b) 1-Disorder_2- (3-fluoro-4-cyanophenyl) -6- (trans4- Synthesis of cyclohexyl) naphthalene "Soluble the entire amount of 1-fluoro-2- (3- I-4-fluorocarboxic acid phenyl) -6- (trans 4-propylcyclohexyl) naphthalene obtained in (IO-a) To 100 ml of acetonitrile, dibromobis (triphenylphosphine) nickel (IIM.2g, triphenylphosphine 1g, zinc at 0.25g, potassium cyanide 6.2g, and added at 8 ° C) ^ Hour. Add 20ml of water to stop the depot, and then use K9n plant ^ 16 J a A ^ &quot; Yu Ji washed the organic layer with 20ml of water for a while, and then dehydrate and dry the refined ..., water & sodium. Purification using silane / dichloromethane = 6/4), branze r ^ $ / ^ ^ ^ R. 9. '…, And then ethanol was recrystallized to obtain 5-fluoro 6-phenyl 2- (anti- 4-Propylcyclohexyl) naphthalene 14.6 ^. The following compounds can also be obtained. 5-fluoro-6-cyano-2- (trans 4-ethylcyclohexyl) naphthalene 5-fluoro-6-cyano-2_ (trans 4-butanecyclohexyl) naphthalene 5-fluoro-6-cyano-2- (Trans 4-pentylcyclohexyl) naphthalene 5-fluoro-6-cyano-2- (trans 4-hexylcyclohexyl) ^ 5-gas-6-cyano-2- (trans 4-heptylcyclohexyl) ^ [ Example 11] Bu 2- (3, 5—synthesis of stubborn earth / prepared-glycine and hexyl) naphthalene—rat—4-randomyl) -6- (trans 4-propane

Page 141 528794

Propylcyclohexane-difluoro, filled with benzyl 'for this hour. Take its water and saturated silica gel to crystallize hexyl)

Make 10 g of 2- (4-aminomethylamino ~ 3 5 mono) naphthalene (this compound will implement '= difluorophenyl) -6- (4-transbenzyl) -6- (trans 4-Propylcyclohexyl) naphthyl fluorene-2 — (3, 5 carbon dioxide to make benzoic acid, complex lithium lithium to metal lithiation and chlorination, and then filling with ammonia gas and sulfur base Add 5ml of oxychloride to make it soluble). Inject the reaction solution into ice water, and then carry out the reaction at a temperature of 2 ° C. Organic layer, water, saturated sodium bicarbonate; : == Tiaohou 'by using anhydrous sodium sulfate dehydration and dry two chromatographic method (hexane / dichloromethane = 6/4) to obtain di-2--2- (3,5-dicyanobenzine: postmortem cadaver Naphthalene 7 Leptyl) -6- (trans 4-propane) can also obtain the following compounds. [1- I-2- (3,5-1-fluoro-2- (3, 5-1-Gas-2 -(3,5-1-Ga-2- (3,5-1-fluoro-2- (3,5-monofluoro-4-cyanophenyl- (transethylcyclohexyl) naphthalene monofluoro-4-cyano Phenyl) —β- (trans 4 -but-cyclohexyl) naphthalenedifluoro-4-cyanophenyl) -6 — (trans 4-pentylcyclohexyl) naphthalenedifluoro-4-cyanophenyl) -6- (trans 4-hexylcyclohexyl) naphthalene difluoro-4-cyanophenyl) -6- (trans 4-heptylcyclohexyl Naphthalene Example 12] 2- (3,4-difluorophenyl) -6 - Synthesis of prop-naphthalene (12-a) 6_ (3,4 - two IL-phenyl) -2 - naphthalene hope of

For 25.0 g of 6-bromo-2-naphthol and 22.0 g of 3,4-difluorobenzylboronic acid, 100 ml of methylbenzyl, 50 ml of ethanol, 50 mi of a 2N potassium carbonate aqueous solution, and 1 bar of (triphenylphosphine) 1 bar were added. (0) 1 · 3 g and heat to reflux for 3 hours. After cooling to room temperature, the organic layer was separated and washed with water and saturated brine. Anhydrous sulfur

Page 142 528794 V. Description of the invention (140) Sodium acid dehydration, dehydration, desulfurization, m ^ b, 彳, 彳, 彳, 彳, 彳 ι, fi μ, using silica gel chromatography (dichloromethane). Tunhua paid 6- (3,4-diphenyl) _2_Cai Fan &amp; 3g. Dimethyl: di-6- (3,4-difluorophenyl) -2-naphthyl ^ ^ Moringa to OvVV &quot; 1 Ben-naphthalene 7.6g dissolved in 30% of the ratio, and the mixture was treated with Moringa While holding down while maintaining the temperature 10. (10 g of trifluoromethanesulfonic anhydride was added dropwise at a rate of 3 or less. After returning to room temperature, followed by stirring for H hours, 50 ml of water was added to this. Extraction was performed with methylene chloride and 100 ml of water. IV, dehydration and drying by anhydrous sodium sulfate, and distilling off the solvent to obtain difluoromethanesulfonated 6- (3,4-difluorophenyl) -2naphthyl U4g. (12 — &gt; 2 — (3 Synthesis of 4,4-difluorophenyl) -6- (1-propynyl) naphthalene Sodium trifluoromethanesulfonate 6- (3,4-difluorophenyl) -2naphthyl u · 4g was dissolved in DMF60ml And 20 ml of triethylamine, and then added (triphenylphosphine) palladium (〇) 〇 · copper iodide (I) 0 · 1 g, the methyl acetylene was introduced under normal temperature and pressure while stirring. It was neutralized with% hydrochloric acid, extracted with toluene 1001111, and washed with water and saturated brine. The solvent was distilled off and purified by silica gel chromatography (hexane) to obtain 2- (3,4-di Fluorophenyl) -6- (1-propynyl) naphthalene 74§. ,, (12 d) 2 (3,4-IL-phenyl) -6-propylnaphthalene Synthesis of 2- (3, 4- 7.4 g of difluorophenyl) -6- (1-propynyl) naphthalene was dissolved in 80 ml of ethyl acetate, 1.5 g of 5% palladium carbon was added, and hydrogen was added in Introduced under normal pressure and stirred for 6 hours. The catalyst was removed by filtration, and the solvent was distilled off to obtain 23 4-difluorophenyl) -6-propylnaphthalene 7. 2g. This was recrystallized by ethanol ,; To the purified product 4.2 g. Cr62. 5 I ^ [实施 例 13] The synthesis of 2- (3, 4, 5-trifluorophenyl) -6-propane naphthalene was used in Example 12, except that 3, 4 were used. , 5-trifluorophenylboronic acid in place of 3, 4-page 143 528794 V. Description of the invention (141)

Except for difluorophenylboronic acid, the same procedure was performed, and 7-bromo-2-naphthol was obtained from 7 g of 2- (3,4,5-trifluorophenyl) -6-propylnaphthalene. 7 Cr50 I The following compounds can be synthesized in the same manner as 12 and 13. 2- (3,4-diIt phenyl) -6-ethylnaphthalene 2- (3,4-difluorophenyl) -6-butylnaphthalene 2- (3,4-difluorophenyl) -6-pentyl Naphthalene 2- (3,4-difluorophenyl) -6-hexylnaphthalene 2- (3,4-difluorophenyl) -6-heptaphthalene 2- (3,4-diphenylphenyl) -6- (3-Butyl) naphthalene

2- (3,4,5-trifluorophenyl) -6-ethylnaphthalene 2- (3,4,5-triILphenyl) -6-propylnaphthalene 2- (3,4,5-trifluorobenzene ) -6-Butylnaphthalene 2- (3,4,5-trifluorophenyl) -6-pentaphthalene 2- (3,4,5-trifluoroiphenyl) -6-hexylnaphthalene 2- (3 , 4,5-trifluorophenyl) -6-heptaphthalene 2- (3,4,5-tri-IL phenyl) -6- (3-butlyl) naphthalene 2- (4-fluorophenyl) -6 -Ethylnaphthalene 2- (4-gasphenyl) -6-propylnaphthalene

2- (4-Gaphthyl) -6-butylnaphthalene 2- (4-benzyl-pentaphthalene 2- (4-gasphenyl) -6-hexylnaphthalene 2-(4-fluorophenyl) -6 -Heptaphthalene 2- (4-gasphenyl) -6- (3-butane) qin 2- (3- Iphenyl) -6-ethyn

Page 144 528794 V. Description of the invention (142) 2- (3-fluorophenyl) -6-propylnaphthalene 2- (3-fluorophenyl) -6-butylnaphthalene 2- (3-fluorobenzyl) -6 -Pentaphthalene 2- (3-fluorophenyl) -6-hexylnaphthalene 2- (3-fluorophenyl) -6-heptaphthalene 2- (3-fluorophenyl) -6- (3-butynyl) Naphthalene 2- (3, 5-difluorophenyl) -6-ethylnaphthalene 2- (3, 5-difluorophenyl) -6-propylnaphthalene 2- (3, 5-difluorophenyl) -6- Butadiene

2- (3, 5-difluorophenyl) -6-pentaphthalene 2- (3, 5-difluorophenyl) -6-hexylnaphthalene 2- (3, 5-difluorophenyl) -6_heptane Naphthalene 2- (3,5-difluorophenyl) -6- (3-butenyl) naphthalene 2-phenyl-6-ethoxy-2-naphthalene 2-phenyl-6-propylnaphthalene 2-phenyl-6-butyl Naphthalene 2-phenyl-6-pentaphthalene

2-phenyl-6-heptaphthalene 2-phenyl-6- (3-butane) naphthalene 2- (4-chlorophenyl) -6-ethynqin 2- (4-chlorophenyl) -6- Propylene Naphthalene 2- (4-chlorophenyl) -6-Butylnaphthalene 2- (4-chlorophenyl) -6-pentan

Page 145 528794 V. Description of the invention (143) 2- (4-chlorophenyl) -6-hexylnaphthalene 2- (4-chlorophenyl) -6-heptaphthalene 2- (4-chlorophenyl) -6 -(3-Butylene) naphthalene 2- (3- | L_4-chlorophenyl) -6-ethylnaphthalene 2- (3-an-4-chlorophenyl) -6-propylnaphthalene 2- (3-fluoro 4-Chlorophenyl) -6-butylnaphthalene 2- (3-Ga-4-chlorophenyl) -6-pentaphthalene 2- (3-Ga-4-chlorophenyl) -6-hexylnaphthalene 2- (3-Fluoro-4-chlorophenyl) -6-heptaphthalene

2- (3-fluoro-4-chlorophenyl) -6- (3-butenyl) naphthalene 2- (3,5-difluoro-4_chlorophenyl) -6-ethoxy 2- (3, 5-Diquinol-4-chlorophenyl) -6-propylnaphthalene 2- (3,5-difluoro-4-chlorophenyl) -6-butylnaphthalene 2- (3,5-diIL-4-chloro Phenyl) -6-pentaphthalene 2- (3,5-di11-4-chlorophenyl) -6-hexylnaphthalene 2- (3,5-didi-4-chlorophenyl) -6-heptaphthalene 2- (3,5-difluoro-4-chlorophenyl) -6- (3-butenyl) naphthalene 2- (4-trifluoromethoxyphenyl) -6-ethylnaphthalene

2- (4-trifluoromethoxyphenyl) -6-propylnaphthalene 2- (4-trifluoromethoxyphenyl) -6-butylnaphthalene 2- (4-trifluoromethoxyphenyl) _6-pentaphthalene 2- (4-trifluoromethoxyphenyl) -6-hexylnaphthalene 2- (4-trifluorofluorenyloxyphenyl) -6-heptaphthalene 2- (4-trifluorofluorenyloxy) -6- ( 3-butenyl) naphthalene

Page 146 528794 V. Description of the invention (144) 2-(3-fluoro-4-trifluorofluorenyloxyphenyl) -6-ethylnaphthalene 2- (3-fluoro-4-trifluoromethoxyphenyl) -6 -Proline naphthalene 2-(3-fluoro-4 -trifluorofluorenyloxyphenyl) -6 -butylnaphthalene 2-(3-gas-4-trifluoromethoxyphenyl) -6 -pentaphthalene 2-(3- Dun-4 -trifluoromethoxyphenyl) -6 -Hexin 2-(3-Ga-4-trigasmethoxyphenyl) -6-Heptan 2- (3- IL-4 -Trifluorophosphonium Phenyl) -6- (3-butylfluorenyl) naphthalene 2- (3,5-difluoro-4-trifluoromethoxyphenyl) -6-ethylnaphthalene 2- (3,5-difluoro-4- Trifluoromethoxyphenyl 6-propylnaphthalene

2-(3, 5 -difluoro-4 -trifluorofluorenyloxyphenyl)-6 -butylnaphthalene 2-(3, 5 -difluoro-4-trifluorofluorenyloxyphenyl 6 -pentaphthalene 2- (3 , 5 -difluoro-4 -tridecanophenoxyphenyl) -6-hexyl-2- (3, 5 -difluoro-4 -trifluoromethoxyphenyl 6-heptaphthalene 2- (3, 5 -di Fluoro-4-trifluorofluorenyloxyphenyl) -6- (3-butenyl) naphthalene 2- (4-difluoromethoxyphenyl) -6-ethylnaphthalene 2- (4-difluoromethoxyphenyl ) -6-propylnaphthalene 2- (4-difluorofluorenyloxyphenyl) -6-butylnaphthalene 2- (4-difluorofluorenyloxyphenyl) -6-pentaphthalene

2- (4-Dimethoxymethoxyphenyl) -6-hexylnaphthalene 2- (4-difluoromethoxyphenyl) -6-heptaphthalene 2- (4-difluoromethoxyphenyl) -6-( 3-Butyl) naphthalene 2-(3-fluoro-4-difluoromethoxyphenyl) -6-ethylnaphthalene 2- (3-fluoro-4 -difluorofluorenoxyphenyl) -6-propylnaphthalene 2 -(3-Ga-4 -Difluorofluorenoxyphenyl 6-butane

Page 147 528794 V. Description of the invention (145) 2- (3-fluoro-4-difluoromethoxyphenyl) -6-pentaphthalene 2- (3-fluoro-4-difluoromethoxyphenyl) -6 -Hexaphthalene 2-(3-4-difluoromethoxyphenyl) -6-heptaphthalene 2-(3-H -4-difluoromethoxyphenyl) -6- (3 -butane) naphthalene 2 -(3, 5-difluoro-4 -difluoromethoxyphenyl) -6-ethylnaphthalene 2- (3, 5 -difluoro-4-difluoroamidooxyphenyl 6-propylnaphthalene 2-(3, 5-di-IL-4 -difluorofluorenyloxyphenyl) -6-butylene 2- (3,5-difluoro-4 -difluorofluorenyloxyphenyl) -6-pentaphthalene 2- (3,5- Difluoro-4-difluoroα-fluorenylphenyl) -6-hexylnaphthalene 2- (3, 5-difluoro-4-difluorofluorenyloxyphenyl) -6-heptaphthalene 2- (3,5-di Fluoro-4-difluoromethoxyphenyl) -6- (3-butenyl) naphthalene 2- (4- (3, 4-difluorophenyl) phenyl) -6-ethylnaphthalene 2- (4- (3,4-difluorophenyl) phenyl) -6-propanenaphthalene 2- (4- (3,4-difluorophenyl) phenyl) -6-butylnaphthalene 2- (4- (3,4 -Difluorophenyl) phenyl) -6-pentaphthalene 2- (4- (3,4-diItphenyl) phenyl) -6-hexylnaphthalene 2- (4- (3, 4-difluorobenzene) ) Phenyl) -6-heptaphthalene 2- (4- (3,4-difluorophenyl) phenyl) -6- (3-butanyl) naphthalene 2- (4- (3,4,5 -Trifluorobenzene ) Phenyl) -6-ethylnaphthalene 2- (4- (3,4,5-tritriphenyl) phenyl) -6-propylnaphthalene 2- (4- (3,4,5-trifluorophenyl) ) Phenyl) -6-butylnaphthalene 2- (4- (3,4,5-trifluorophenyl) phenyl) -6-pentaphthalene 2- (4- (3,4,5-trifluorophenyl) ) Phenyl) -6-hexylnaphthalene 2- (4- (3,4,5-trifluorophenyl) phenyl) _6-heptaphthalene

Page 148 528794 V. Description of the invention (146) 2- (4- (3, 4, 5-trifluorophenyl) phenyl) -6- (3-butanyl) naphthalene 2- (4- (4- Fluorophenyl) phenyl) -6-ethylnaphthalene 2- (4- (4-fluorophenyl) phenyl) -6-propylnaphthalene 2- (4_ (4-fluorophenyl) phenyl) -6_butylnaphthalene 2- (4- (4-fluorophenyl) phenyl) -6-pentaphthalene 2- (4- (4-fluorophenyl) phenyl) -6-hexylnaphthalene 2- (4- (4-fluorobenzene ) Phenyl) -6-heptaphthalene 2- (4- (4-fluorophenyl) phenyl) -6- (3-butane) naphthalene 2- (4- (3-fluorophenyl) phenyl)- 6- Yiqin

2- (4- (3- (phenyl) phenyl) phenyl) -6-propanthine 2- (4- (3-fluorophenyl) phenyl) -6-butylene 2- (4- (3-gasbenzene) Phenyl) -6-pentaphthalene 2- (4- (3-fluoroαphenyl) phenyl) -6-hexylnaphthalene 2- (4- (3-fluorophenyl) phenyl) _6-heptaphthalene 2- (4- (3-fluorophenyl) phenyl) -6- (3-butlyl) naphthalene 2_ (4- (3,5-diItphenyl) phenyl) -6-ethylnaphthalene 2- (4- (3,5-difluorophenyl) phenyl) -6-propylnaphthalene 2- (4- (3,5-difluorophenyl) phenyl) -6-butylene

2- (4- (3,5-difluorophenyl) phenyl) -6-pentaphthalene 2- (4- (3,5-difluorophenyl) phenyl) -6-hexylnaphthalene 2- (4_ (3,5-difluorophenyl) phenyl) -6-heptan-2- (4- (3,5-difluorophenyl) phenyl) -6- (3-butenyl) naphthalene 2- ( 4- (4-chlorophenyl) phenyl) -6-ethylnaphthalene 2- (4- (4-chlorophenyl) phenyl) -6-propanine

Page 149 528794 V. Description of the invention (147) 2- (4- (4-chlorophenyl) phenyl) -6-butylnaphthalene 2- (4- (4-chlorophenyl) phenyl) -6-pentyl Naphthalene 2- (4- (4-chlorophenyl) phenyl) -6-hexylnaphthalene 2- (4- (4-chlorophenyl) phenyl) -6-heptaphthalene 2- (4- (4-chloro Phenyl) phenyl) -6- (3-butenyl) naphthalene 2- (4- (3-Dun-4-chlorophenyl) phenyl) -6-ethylnaphthalene 2- (4- (3-fluoro -4-chlorophenyl) phenyl) -6-propylnaphthalene 2- (4- (3-fluoro-4 -chlorophenyl) phenyl) -6 -butylnaphthalene 2- (4- (3-fluoro-4 -Chlorophenyl) phenyl) -6-pentaphthalene

2- (4- (3-Dun-4-chlorophenyl) phenyl) -6-hexyl-2- (4- (3-fluoro-4-chlorophenyl) phenyl) -6-heptaphthalene 2- ( 4- (3-fluoro-4-chlorophenyl) phenyl) -6- (3-butanyl) naphthalene 2- (4- (3,5-difluoro-4-chlorophenyl) phenyl)- 6-Ethylnaphthalene 2- (4- (3,5-diH-4-chlorophenyl) phenyl) -6-propylnaphthalene 2- (4- (3, 5-difluoro-4-chlorophenyl) Phenyl) -6-butylene 2- (4- (3,5-digas-4-chlorophenyl) phenyl) -6-pentaphthalene 2- (4- (3,5-difluoro4-chloro Phenyl) phenyl) -6-hexylnaphthalene 2- (4- (3,5-di-Jin-4-chlorophenyl) phenyl) -6-heptaphthalene

2- (4- (3, 5-difluoro-4-chlorophenyl) phenyl) -6- (3-butenyl) naphthalene 2- (4- (4-trifluorofluorenyloxy) phenyl -6-Ethylnaphthalene 2-(4- (4-trifluoromethoxyphenyl) phenyl-6-propylnaphthalene 2- (4- (4-trifluoromethoxyphenyl) phenyl-6-butylnaphthalene 2 -(4- (4-trifluorofluorenyloxyphenyl) phenyl-6-pentaphthalene

Page 150 528794 V. Description of the invention (148)

2- (4- (4-trifluoromethoxyphenyl) phenyl-6-heptaphthalene 2- (4- (4-trifluoromethoxyphenyl) phenyl-6- (3-butenyl) naphthalene 2-(4- (3-fluoro-4 -trifluoromethoxyphenyl) phenyl) -6-ethylnaphthalene 2- (4- (3-fluoro-trifluoromethoxyphenyl) phenyl) -6- Propylnaphthalene 2- (4- (3-fluoro-4 -trifluorofluorenyloxyphenyl) phenyl) -6-butylnaphthalene 2- (4- (3-H-4 -trifluoromethoxyphenyl) phenyl ) -6-pentaphthalene 2- (4- (3-fluoro-4 -trifluoromethoxyphenyl) phenyl) -6-hexylnaphthalene 2- (4- (3-fluoro-4-trifluoromethoxybenzene) Phenyl) -6-heptaphthalene 2- (4- (3-fluoro-4 -trifluoromethoxyphenyl) phenyl) -6- (3 -butane) naphthalene 2- (4-(3 , 5 -difluoro-4 -tris Itoxophenyl) phenyl) -6-ethylnaphthalene 2- (4- (3,5-difluoro-4 -trigasmethoxymethoxy) phenyl) -6 -Propylnaphthalene 2- (4- (3,5-di-It-4 -tri-Itoxophenyl) phenyl) -6-butyphthalene 2- (4- (3,5 -digas-4 -tridecane Phenoxyphenyl) phenyl) -6-pentaphthalene 2- (4- (3,5-difluoro-4-trifluorofluorenyloxyphenyl) phenyl) -6-hexylnaphthalene 2-(4-(3 , 5-difluoro-4-trifluorofluorenyloxyphenyl) phenyl) -6-heptaphthalene 2- (4- (3,5-di4-trifluorofluorenyloxyphenyl) phenyl) -6- ( 3-Tingji Naphthalene

2- (4- (4-DiIL 曱 oxophenyl) phenyl) -6-ethylnaphthalene 2- (4- (4-difluoro 曱 oxophenyl) phenyl) -6-propylnaphthalene 2-(4 -(4-difluorofluorenyloxyphenyl) phenyl) -6-butylnaphthalene 2- (4- (4-difluoromethoxyphenyl) phenyl) -6-pentaphthalene 2- (4- (4- Dimethoxymethoxyphenyl) phenyl) -6-hexylnaphthalene 2- (4- (4-difluoromethoxyphenyl) phenyl) -6-heptaphthalene 2- (4- (4-difluorofluorenyloxy) Phenyl) phenyl) -6- (3-butenyl) naphthalene

Page 151 528794 V. Description of the invention (149)

2- (4- (3-deca-4-difluoromethoxyphenyl) phenyl) -6-ethylnaphthalene 2- (4- (3-fluoro-4 -difluoromethoxyphenyl) phenyl)- 6-propylnaphthalene 2-(4- (3-fluoro-4 -di-IL-methoxyphenyl) phenyl) -6-butylnaphthalene 2- (4- (3-fluoro-4 -di-IL-methoxyphenyl) Phenyl) -6-pentaphthalene 2- (4- (3-fluoro-4 -difluoromethoxyphenyl) phenyl) -6-hexylnaphthalene 2- (4- (3-fluoro-4-difluoromethyl) Oxyphenyl) phenyl) -6-heptaphthalene 2- (4- (3-fluoro-4-difluorofluorenyloxyphenyl) phenyl) -6- (3-butanyl) naphthalene 2- (4- (3,5-difluoro-4-difluoromethoxyphenyl) phenyl) -6-ethylnaphthalene 2- (4- (3,5-difluoro-4 -diIL methoxyphenyl) phenyl 6 -Proline naphthalene 2-(4- (3,5 -Diden-4 -difluoromethoxyphenyl) phenyl) -6-butylnaphthalene 2-(4-(3,5-digas-4 -digas Phenoxyphenyl) phenyl) -6-pentaphthalene 2- (4-(3,5-difluoro-4 -difluoromethoxyphenyl) phenyl) -6-hexylnaphthalene 2-(4-(3 , 5-Diden-4 -diItmethoxyphenyl) phenyl) -6-heptaphthalene 2- (4- (3, 5-difluoro-4-difluorofluorenyloxyphenyl) phenyl) -6 -(3-butenyl) naphthalene

2- (4- (4-trifluorotolyl) phenyl) -6-ethaneqin 2- (4- (4-trifluorotolyl) phenyl) -6-propanzine 2- (4- (4 -Trifluorotolyl) phenyl 6-Butylnaphthalene 2- (4- (4-trifluorotolyl) phenyl) -6-pentyl 2- (4- (4-trifluorophenyl) phenyl) -6-Hexaphthalene 2- (4- (4-trifluorotolyl) phenyl) -6-heptaphthalene 2- (4- (4-trifluorofluorenyl) phenyl) -6- (3-butane Alkyl) naphthalene 2- (4- (3- 4-trifluorotolyl) phenyl) -6-ethylnaphthalene 2- (4- (3-den-4_trifluorotolyl) phenyl) -6- Pronaphthalene

Page 152 528794 V. Description of the invention (150) 2- (4- (3-fluoro-4-trifluoro i 2- (4- (3-fluoro-4-trifluoro 2- (4- (3-fluoro- 4-trifluoro 2- (4- (3-gas-4-trifluoro 2- (4- (3-fluoro-4 -trifluoro 2-(4-(3,5 -di-it-4-2- ( 4- (3,5-difluoro-4-2- (4- (3,5-difluoro-4-2- (4- (3,5-difluoro-4-2- (4- (3, 5-Difluoro-4-2- (4- (3, 5-difluoro-4-2-(4-(3,5-difluoro-4-2- (4- (4-fluorenoxyphenyl)) 2- (4- (4-Methoxyphenyl) 2- (4- (4-Methoxyphenyl) 2- (4- (4-Methoxyphenyl) 2- (4- (4-Methoxyphenyl) Group) 2- (4- (4-fluorenyloxyphenyl) 2- (4- (4-fluorenyloxyphenyl) 2- (4- (3- I-4-methoxy-2- (4- (3- Fluoro-4-methoxy-2- (4- (3-fluoro-4-methoxy-2- (4- (3-fluoro-4-methoxy-2- (4- (3-fluoro-4-fluorenyltolyl) ) Phenyl) -6-Butylnaphthylphenyl) Phenyl) -6-Pentaphthalenetolyl) Phenyl) -6-Hexylnaphthylbenzyl) Phenyl) -6-Heptaphthyltolyl) phenyl) -6- (3-butenyl) naphthalenetrifluorotolyl) phenyl) -6-ethylnaphthalenetrifluorotolyl) phenyl) -6-propylnaphthalenetrifluorotolyl) phenyl) -6-butylnaphthalene Trifluorotolyl) phenyl) -6-pentaphthalenetrifluorotolyl) phenyl) -6-hexylnaphthalenetrifluorotolyl Phenyl) -6-heptaphthyltriyltolyl) phenyl) -6- (3-butenyl) naphthylphenyl) -6-ethylnaphthylphenyl) -6-propylnaphthylphenyl) -6-butane Naphthylphenyl) -6-pentaphthylphenyl) -6-heptaphthylphenyl) -6-heptaphthylphenyl) -6- (3-butenyl) naphthylphenyl) phenyl) -6-ethylnaphthalene Phenyl) phenyl) -6-propylnaphthylphenyl) phenyl) -6-butylnaphthylphenyl) phenyl) -6-pentaphthylphenyl) phenyl) -6-hexylnaphthalene

I Page 153 528794 V. Description of the invention (151) 2- (4- (3-fluoro-4-methoxyphenyl) phenyl) -6-heptaphthalene 2- (4- (3- 4-methoxybenzene Phenyl) -6- (3-butenyl) naphthalene 2- (4- (3,5-digas-methoxyphenyl) phenyl) -6-ethylnaphthalene 2- (4-(3, 5-difluoro-4-fluorenyloxyphenyl) phenyl) -6-propylnaphthalene 2- (4- (3,5-difluoro-4-methoxyphenyl) phenyl) -6-butylnaphthalene 2- (4- (3, 5-difluoro-4-oxophenyl) phenyl) -6-pentaphthalene 2- (4- (3,5-difluoro-4-methoxyphenyl) phenyl)- 6-Hexaphthalene 2- (4- (3, 5-difluoro-4-methoxyphenyl) phenyl) -6-heptaphthalene 2- (4- (3,5-difluoro-4-fluorenyloxybenzene) ) Phenyl) -6- (3-butenyl) naphthalene

2- (4- (4-Dilute propoxyphenyl) phenyl) -6-ethynqin 2- (4- (4-dilute propoxyphenyl) phenyl) -6-propylnaphthalene 2- (4- ( 4-Allyloxyphenyl) phenyl) _6-Butylnaphthalene 2- (4- (4-allyloxyphenyl) phenyl) -6-pentaphthalene 2- (4- (4-allyloxyphenyl) ) Phenyl) -6-hexylnaphthalene 2- (4- (4-dipropoxyphenyl) phenyl) -6-heptaphthalene 2- (4- (4-allyloxyphenyl) phenyl) -6 -(3-butenyl) naphthalene 2- (4- (4-fluorenylphenyl) phenyl) -6-ethylnaphthalene 2- (4- (4-fluorenylphenyl) phenyl) -6-propylnaphthalene

2- (4- (4-fluorenylphenyl) phenyl) -6-butylnaphthalene 2- (4- (4-fluorenylphenyl) phenyl) -6-pentaphthalene 2- (4- (4-fluorenebenzene Phenyl) -6-hexylnaphthalene 2- (4- (4-fluorenyl) phenyl) -6-heptaphthalene 2- (4- (4-fluorenyl) phenyl) -6- (3 -Butenyl) naphthalene 2- (4- (4- (3-butenephenyl) phenyl))-6-ethylnaphthalene

Page 154 528794 V. Description of the invention (152) 2- (4- (4- (3-butanephenyl) phenyl))-6-propylnaphthalene 2- (4- (4- (3-butenebenzene Phenyl))-6-butylene 2-naphthalene 2- (4- (4- (3-butylene) phenyl))-6-pentaphthalene 2- (4- (4- (3-butylene) Phenyl))-6-Hexyl 2- (4- (4- (3-butanephenyl) phenyl))-6-heptaphthalene 2- (4- (4- (3-butanebenzene Phenyl))-6- (3-butanyl) Cai 2- (3-fluoro-4- (3,4-difluorophenyl) phenyl) -6-ethylnaphthalene 2- (3_ _4_ (3,4-difluorophenyl) phenyl) -6-propylnaphthalene 2- (3-fluoro-4- (3,4-difluorophenyl) phenyl) -6-butylnaphthalene

2- (3-fluoro-4- (3,4-diphenylphenyl) phenyl) -6-pentaphthalene 2- (3-fluoro-4- (3,4-difluorophenyl) phenyl)- 6-Hexaphthalene 2- (3-fluoro-4 (3,4-difluorophenyl) phenyl) -6-heptaphthalene 2- (3-dun-4- (3,4-di-phenyl) Phenyl) -6- (3-butanyl) qin 2- (3-IL-4- (3,4,5-tritriphenyl) phenyl) -6-ethylnaphthalene 2- (3-gas- 4- (3,4,5-trifluorophenyl) phenyl) -6-propylnaphthalene 2- (3-fluoro-4- (3,4,5-tritriphenyl) phenyl) -6-butane Naphthalene 2- (3-Ga-4- (3,4,5-tri-phenyl) phenyl) -6-pentanqin 2- (3-fluoro-4-(3,4,5-trifluorophenyl) ) Phenyl) -6-hexane

2- (3-fluoro-4- (3,4,5-trifluorophenyl) phenyl) -6-heptaphthalene 2- (3-fluoro-4- (3,4,5-tridunylphenyl) Phenyl) -6- (3-butenyl) naphthalene 2- (3- | 1-4- (4-aerophenyl) phenyl) -6-ethaneqin 2- (3-fluoro-4- (4 -Fluorophenyl) phenyl) -6-propanthine 2- (3-benzyl-4- (4-fluorophenyl) phenyl) -6-butanthine 2- (3-gas-4- (4-fluoro Phenyl) phenyl) -6-pentaphthalene

Page 155 528794 V. Description of the invention (153) Gas-4- (4-fluorofluoro-4- (4-fluoro2- (3-2- (3-2- (3-2- (3-2- ( 3-2- (3-2-(3 -2- (3-2- (3-2- (3-2- (3-2- (3-2- (3-2-(3- dun-4- (4-fluoro It-4- (3-deaton-4- (3-like It-4- (3-deafluoro-4- (3-fluorofluoro-4- (3-fluorofluoro-4- (3-fluorofluoro- 4- (3- H 11-4- (3,5-fluoro-4- (3, δ-ΐΐ-4- (3, 5- 2-(3-fluoro-4- (3,5-2-( 3-2- (3-2- (3- 2-(3-2- (3-2- (3-2- (3-2- (3-fluoro-4- (3,5-H-4- (3,5-fluoro-4- (3, 5-fluoro-4- (4-chlorofluoro-4-(4-chlorofluoro-4- (4-chlorofluoro-4- (4-chlorofluoro-4- (4-chlorophenyl) phenyl) -6-hexylnaphthylphenyl) phenyl) ~~ 6-heptaphthylphenyl) phenyl) -6- (3 -butenyl) naphthylphenyl) phenyl) -6-ethylnaphthylphenyl) phenyl) -6-propylnaphthylphenyl) phenyl) -6-butylnaphthylphenyl) phenyl) -6-pentaphthylphenyl) phenyl) -6-hexanaphthylbenzene ) Phenyl) -6-heptaphthylphenyl) phenyl) -6- (3-butenyl) naphthalenedifluorophenyl) phenyl) -6-ethinaphthyldifluorophenyl) phenyl) -6 -Pinaphthalene difluorophenyl) phenyl) -6-Butylnaphthalenedifluorophenyl) phenyl) -6-Pentaphthalenedifluorophenyl) phenyl) -6-HexaphthalenediIIphenyl) phenyl) -6-heptaphthylbenzene Group) phenyl) -6- (3-butenyl) naphthylphenyl) phenyl) -6-ethethenephenyl) phenyl) -6-propylnaphthylphenyl) phenyl) -6-butylnaphthylbenzene Yl) phenyl) -6-pentaphthylphenyl) phenyl) -6-hexylnaphthalene 2- (3-fluoro-4- (4-chlorophenyl) phenyl) -6-heptan-2- (3-fluoro 4- (4-chlorophenyl) phenyl) -6- (3-butenyl) naphthalene

I Page 156 528794 V. Description of the Invention (154)

2- (3-fluoro-4- (3-gas-4-chlorophenyl) phenyl) -6-ethylnaphthalene 2- (3-fluoro-4- (3-It-4-chlorophenyl) phenyl ) -6-propylnaphthalene 2- (3-decan-4- (3-fluoro-4-chlorophenyl) benzyl) -6-butylnaphthalene 2- (3-fluoro-4- (3-fluoro-4- Chlorophenyl) phenyl) -6-pentaphthalene 2- (3-fluoro-4- (3-fluoro-4-chlorophenyl) phenyl) -6-hexylnaphthalene 2- (3-fluoro-4- ( 3 -fluoro-4-chlorophenyl) phenyl) -6-heptaphthalene 2- (3-fluoro-4- (3-fluoro-4-chlorophenyl) phenyl) -6- (3 -butylfluorenyl ) Naphthalene 2- (3-fluoro-4- (3,5-di4-chlorophenyl) phenyl) -6-ethylnaphthalene 2- (3-fluoro-4- (3,5-dioxo-4- Chlorophenyl) phenyl) -6-propylnaphthalene 2- (3-fluoro-4- (3,5-digas-4-chlorophenyl) phenyl) -6-butylnaphthalene 2- (3-fluoro- 4- (3,5-Didi-4-chlorophenyl) phenyl) -6-pentaphthalene 2- (3-fluoro-4 (3,5-difluoro-4-chlorophenyl) phenyl) -6-Hexaphthalene 2- (3-fluoro-4- (3,5-dibenzyl-4-chlorophenyl) phenyl) -6-heptaphthalene 2- (3-fluoro-4- (3,5- DiIL-4-chlorophenyl) phenyl) -6- (3-butenyl) naphthalene 2- (3-fluoro-4- (4-trifluoromethoxyphenyl) phenyl) -6-ethylnaphthalene 2- (3-Ga-4- (4-trifluoromethoxyphenyl) phenyl) -6-propylnaphthalene 2- (3-fluoro-4- (4-trifluoromethoxyphenyl) phenyl)-6-butylene

2-(3-it-4- (4-trifluoromethoxyphenyl) phenyl) -6-pentaphthalene 2- (3-fluoro-4- (4-trifluoromethoxyphenyl) phenyl)- 6-hexylnaphthalene 2- (3-fluoro-4-(4-trifluorofluorenyloxyphenyl) phenyl) -6-heptaphthalene 2- (3-fluoro-4- (4-trifluoromethoxyphenyl) Phenyl) -6- (3-butenyl) naphthalene 2- (3-fluoro-4- (3-fluoro-4-trifluoromethoxyphenyl) phenyl) -6-ethylnaphthalene 2- (3- Fluoro-4- (3-fluoro-4-trifluorofluorenyloxyphenyl) phenyl) -6-propylnaphthalene

Page 157 528794 V. Description of the invention (155) 2- (3-Fluoro-4- (3-fluoro-4 -trioxophenyl) phenyl) -6-butylnaphthalene 2- (3-decan-4- (3-Fluoro-4 -trifluorofluorenyloxyphenyl) phenyl 6-pentaphthalene 2- (3-fluoro-4- (3-fluoro-4 -trioxoloxyphenyl) phenyl) _6-hexanaphthalene 2- (3-fluoro-4-(3-fluoro-4 -trifluoromethoxyphenyl) phenyl) -6-heptaphthalene 2- (3-benzyl-4- (3-benzyl-4 -trifluorofluorene) Oxyphenyl) phenyl) -6- (3-butanyl) naphthalene 2- (3-fluoro-4-(3,5 -digas-4 -trifluoromethoxyphenyl) phenyl) -6- Ethylnaphthalene 2- (3-fluoro-4- (3,5-difluoro-4 -trifluorofluorenoxyphenyl) phenyl 6-propylnaphthalene 2- (3-fluoro-4- (3,5-difluoro -4-trifluoromethoxyphenyl) phenyl) -6-butylene 2- (3-gas-4- (3,5-difluoro-4-trifluoromethoxyphenyl) phenyl) -6- Pentaphthalene 2- (3-fluoro-4- (3,5-difluoro-4-trifluorofluorenyloxyphenyl) phenyl) -6-hexylnaphthalene 2- (3-benzyl-4- (3,5- Difluoro-4-trifluoromethoxyphenyl) phenyl) -6-heptaphthalene 2- (3-dun-4- (3,5-difluoro-4 -trifluoromethoxyphenyl) phenyl)- 6- (3-butenyl) naphthalene 2- (3-fluoro-4- (4-difluorofluorenyloxyphenyl) phenyl) -6-ethylnaphthalene 2- (3--4- (4-diIt Methoxyphenyl) phenyl) -6-propylnaphthalene 2 -(3-fluoro-4- (4-difluorofluorenyloxyphenyl) phenyl) -6-Ding Qin 2- (3- l-4- (4-difluorofluorenyloxyphenyl) phenyl) -6 -Pentaphthalene 2- (3-fluoro-4- (4-difluorofluorenyloxyphenyl) phenyl) -6-hexylnaphthalene 2- (3-fluoro-4-(4-difluorofluorenyloxyphenyl) benzene ) -6-heptaphthalene 2- (3--(4-diIImethoxyphenyl) phenyl) -6- (3-butenyl) naphthalene 2- (3-fluoro-4- (3-gas -4 -Diaphthyloxyphenyl) phenyl) -6-ethylnaphthalene 2-(3-fluoro-4- (3-gas-4 -difluoromethoxyphenyl) phenyl) -6-propylnaphthalene 2 -(3-Gas-4- (3-Fluoro-4 -difluoromethoxyphenyl) phenyl) -6-butylnaphthalene 111 Page 158 528794 5. Description of the invention (156) 2- (3-Gas-4 -(3-Ga-4-diItmethoxyphenyl) phenyl) -6-pentaphthalene 2- (3-fluoro-4- (3-fluoro-4-diItmethoxyphenyl) phenyl)- 6-Hexaphthalene 2- (3-fluoro-4 (3-fluoro-4 -difluoromethoxyphenyl) phenyl) -6-heptaphthalene 2- (3-fluoro-4- (3-deca-4 -Difluoromethoxyphenyl) phenyl) -6- (3-butenyl) naphthalene 2- (3-fluoro-4- (3,5-difluoro-4-difluoro-i-methoxyphenyl) benzene 6-Ethylnaphthalene 2- (3-benzyl-4- (3,5-difluoro ^ 4-difluorofluorenyloxyphenyl) phenyl) -6-propylnaphthalene 2- (3 -benzyl-4-(3 , 5 -difluoro-4 -difluoromethyl Oxyphenyl) phenyl) -6-butylnaphthalene 2- (3-fluoro ^ 4- (3,5-difluoro4-difluorofluorenyloxyphenyl) phenyl) -6-pentaphthalene 2- (3- Fluoro-4- (3, 5-difluoro-4-difluorofluorenyloxyphenyl) phenyl) -6-hexylnaphthalene 2- (3-fluoro-4- (3,5-digas-4-di-IL) (Methoxyphenyl) phenyl) -6-heptaphthalene 2- (3-fluoro-4- (3,5-difluoro-4-difluoromethoxyphenyl) phenyl) -6- (3-butene ) Naphthalene 2- (3-fluoro-4-(4-trifluorofluorenyl) phenyl) -6-ethylnaphthalene 2- (3-fluoro-4- (4-trifluorotolyl) phenyl 6- Propylene Naphthalene 2- (3-Fluoro-4- (4-trifluorotolyl) phenyl) -6-butylnaphthalene 2- (3-fluoro-4- (4-trifluorotolyl) phenyl) -6- Pentaphthalene 2- (3-fluoro-4-(4-trifluorotolyl) phenyl) -6-hexylnaphthalene 2-(3-gas-4-(4-trifluorotolyl) phenyl 6-heptaphthalene 2- (3-fluoro-4- (4-trifluorotolyl) phenyl) -6- (3-butenyl) naphthalene 2- (3--4-(3-fluoro-4 -trifluorotolyl) ) Phenyl) -6-ethylnaphthalene 2- (3-fluoro-4- (3-fluoro-4-trifluorotolyl) phenyl) -6-propylnaphthalene 2- (3-fluoro-4- (3- -4-trioxophenyl) phenyl) -6-butylnaphthalene 2- (3-fluoro-4- (3-fluoro-4 -trifluorotolyl) phenyl) -6-pentaphthalene

Page 159 528794 V. Description of the invention (157) 2- (3-fluoro-4- (3-fluoro-4-trifluorotolyl) phenyl) -6-hexylnaphthalene 2-(3-gas-4-( 3-fluoro-4 -trifluorotolyl) phenyl) -6 -heptaphthalene 2- (3-fluoro-4- (3-fluoro-4 -tri-IL-phenyl) phenyl) -6- (3- Butenyl) naphthalene 2- (3-benzyl-4- (3,5-difluorotrifluorofluorenylphenyl) phenyl) -6-ethynqin 2- (3-Jiu-4- (3,5-di Fluoro-4 -trifluorofluorenyl) phenyl) -6-propylnaphthalene 2- (3-4- (3,5 -difluoro-4 -trifluorotolyl) phenyl) -6 -butylnaphthalene 2- (3-4- (3,5-diH-4 -trifluorophenyl) phenyl) -6-pentaphthalene 2-(3-fluoro-4 4- (3,5-difluoro-4 4-trifluoro Stilbene) phenyl) -6-hexylnaphthalene 2- (3-IL-4- (3,5-difluoro-4-trifluorotolyl) phenyl) -6-heptaphthalene 2- (3-fluoro -4- (3,5-difluoro-4 -tri-II fluorenyl) phenyl) -6- (3-butenyl) naphthalene 2- (3- 4- (4-methoxyphenyl) phenyl ) -6-Ethylnaphthalene 2- (3-fluoro-4-(4-methoxyphenyl) phenyl 6-propylnaphthalene 2- (3- I-4- (4-methoxyphenyl) phenyl)- 6-Butylnaphthalene 2- (3-fluoro-4-(4-methoxyphenyl) phenyl) -6-pentan-2- (3-benzyl-4-(4-methoxyphenyl Phenyl) -6-hexyl 2- (3-fluoro-4- (4-methoxyphenyl) phenyl) -6-heptaphthalene 2- (3 ~ gas-4- (4-methoxyphenyl) Phenyl) -6- (3-butanyl) qin 2- (3-fluoro-4- (3-gas-4- (methoxyphenyl) phenyl) -6-ethylnaphthalene 2- (3-fluoro -4- (3-Gas-4- (methoxyphenyl) phenyl) -6-propanephthalene 2- (3-fluoro-4- (3-fluoro-4- (methoxyphenyl) phenyl) -6 -Ding Qin 2- (3-fluoro-4- (3-dun-4- (methoxyphenyl) phenyl) -6-pentaphthalene 2- (3 ~ fluoro-4- (3-fluoro-4- ( Phenoxyphenyl) phenyl) -6-hexane

Page 160 528794 V. Description of the invention (158) 2- (3-2- (3 -2-(3 -2- (3-2- (3-2- (3-2- (3-2- (3-2- (3 -2-(3-based) Qin 2- (3-2-(3 -2- (3-2- (3-2- (3-2- (3-2- (3-2- (3-2 (3-2 -(3-2-(3 -2-(3 -2- (3-2-(3-2- (3- IL-4- (3-defeated-4-(3 -IL-4- (3, IL-4-(3, fluoro-4- (3, fluoro-4- (3, fluoro-4- (3, fluoro-4--(3, fluoro-4- (3, fluoro-4- (methoxybenzene) ) Phenyl) -6-heptaphthylfluoro-4- (methoxyphenyl) phenyl) -6- (3-butenyl) naphthalene 5-difluoro-4-oxophenyl) phenyl)- 6-Ethylnaphthalene 5-difluoro-4-methoxyphenyl) phenyl) -6-propylnaphthalene 5-difluoro-4-methoxyphenyl) phenyl) -6-butylnaphthalene 5-difluoro-4 -Methoxyphenyl) phenyl) -6-pentaphthalene 5-difluoro-4-oxophenyl) phenyl) -6-hexylnaphthalene 5-difluoro-4-methoxyphenyl) phenyl)- 6-heptaphthalene 5-difluoro-4-methoxyphenyl) phenyl) -6-(3-butenefluoro-4- (4-enfluoro + (4-enfluoro-4- (4-enfluoro) -4- (4-enfluoro-4- (4-enfluoro-4- (4-ene-4)-(4-dichloro-4- (4-methylfluoro-4 (4-methylfluoro-4 -(4-methylfluoro-4-(4-methylfluoro-4- (4-formamidine α-4-(4-methylIL-4- (4-methylpropoxyphenyl) phenyl) -6-ethylnaphthalene Propoxyphenyl) Phenyl) -6-Pronaphthylpropoxyphenyl) Phenyl) -6-Butylnaphthylpropoxyphenyl) Phenyl) -6-Pentaphthylpropoxyphenyl) Phenyl) -6-Hexylnaphthopropoxyphenyl ) Phenyl) -6-heptaphthylpropoxyphenyl) phenyl) -6- (3-butenyl) naphthylphenyl) phenyl) -6-ethinaphthylphenyl) phenyl) -6-propyl Naphthylphenyl) phenyl) -6-butylnaphthylphenyl) phenyl) -6-pentaphthalenephenyl) phenyl) -6-hexylnaphthylphenyl) phenyl) -6-heptaphthylphenyl) phenyl ) -6- (3-butylene) naphthalene

Page 161 528794 V. Description of the invention (159) 2- (3- IL-4- (4- (3-butanephenyl) phenyl))-6-ethylnaphthalene 2- (3- IL-4- ( 4- (3 * butyl diphenyl) phenyl))-6-propylnaphthalene 2- (3-fluoro-4- (4- (3-butenephenyl) phenyl))-6-butylnaphthalene 2- (3-Fluoro-4- (4- (3-butanephenyl) phenyl))-6-pentaphthalene 2- (3-Ga-4- (4- (3-butanephenyl) phenyl) ) -6-hexylnaphthalene 2- (3-fluoro-4- (4- (3-butenephenyl) phenyl))-6-heptaphthalene 2- (3-fluoro-4- (4- (3- Butyl phenyl) phenyl))-6- (3-Butyl) naphthalene 2- (3,5-difluoro-4-(3,4-difluorophenyl) phenyl) -6-ethylnaphthalene 2-(3,5-di 4- (3,4-difluorophenyl) phenyl) -6-propylnaphthalene

2- (3,5-difluoro-4- (3,4-difluorophenyl) phenyl) -6-butylene 2- (3,5-digas-4- (3,4-diIL benzene) Phenyl) -6-pentaphthalene 2- (3,5-difluoro4- (3,4-difluorophenyl) phenyl) -6-hexylnaphthalene 2- (3,5-difluoro-4 -(3,4-difluorophenyl) phenyl) -6-heptaphthalene 2- (3,5-difluoro-4- (3,4-difluorophenyl) phenyl) -6- (3- Butanyl) naphthalene 2- (3,5-difluoro-4-(3,4,5-trifluorophenyl) phenyl) -6-ethanezine 2- (3, 5-difluoro-4- ( 3,4,5-trifluorophenyl) phenyl) -6-propylnaphthalene 2- (3,5-difluoro-4- (3,4,5-trifluorophenyl) phenyl) -6-butane Naphthalene 2- (3, 5-difluoro-4- (3, 4,5-trifluorophenyl) phenyl) -6-pentaphthalene 2- (3, 5-difluoro-4- (3, 4, 5-trifluorophenyl) phenyl) -6-hexylnaphthalene 2- (3,5-diden-4- (3,4,5-trifluorophenyl) phenyl) -6-heptaphthalene 2- ( 3,5 -Ditown-4_ (3,4,5-trifluorophenyl) phenyl) -6- (3_butenyl) naphthalene 2- (3,5-difluoro-4- (4-ILbenzene Phenyl) -6-ethylnaphthalene 2- (3,5-difluoro-4- (4-Gaphenyl) phenyl) -6-propylnaphthalene

Page 162 528794 V. Description of the invention (160) 2-(3,5-difluoro-4- (4-IIphenyl) phenyl) -6-butadiene 2- (3,5-dijiu-4- (4-fluorophenyl) phenyl) -6-pentaphthalene 2- (3,5-difluoro-4- (4-fluorophenyl) phenyl) -6-hexylnaphthalene 2- (3,5-di IL-4- (4-fluorophenyl) phenyl) -6-heptaphthalene 2- (3,5-diden-4- (4-fluorophenyl) phenyl) -6- (3-butanyl ) Naphthalene 2- (3,5-digas-4- (3-gasphenyl) phenyl) -6-ethylnaphthalene 2- (3,5-difluoro-4- (3-decylphenyl) phenyl ) -6-propylnaphthalene 2- (3,5-difluoro-4- (3-fluorophenyl) phenyl) -6-butylene naphthalene 2- (3,5-difluoro-4- (3-fluorobenzene Phenyl) -6-pentaphthalene 2- (3,5-di 4- (3-Gaphenyl) phenyl) -6-hexamethylene 2- (3,5-difluoro-4- (3- Fluorophenyl) phenyl) -6-heptaphthalene 2- (3,5-difluoro-4- (3-fluorophenyl) phenyl) -6- (3-butenyl) naphthalene 2- (3, 5 -difluoro-4- (3,5-difluorophenyl) benzyl) -6-ethanezine 2- (3,5-di-5 -difluorophenyl) phenyl) -6-propylnaphthalene 2- (3,5-difluoro-4- (3,5-difluorophenyl) phenyl) -6-butylene 2- (3,5-difluoro-4- (3,5-difluorophenyl) Phenyl) -6-pentaphthalene 2- (3,5-di -4- (3,5-difluorophenyl) phenyl) -6-hexylnaphthalene 2- (3,5-diH-4- (3,5-diItphenyl) phenyl) -6-heptane Naphthalene 2- (3,5-digas-4- (3,5-difluorophenyl) phenyl) -6- (3-butynyl) naphthalene 2- (3,5-di1-4- (4-chlorophenyl) phenyl) -6-ethylnaphthalene 2- (3,5-difluoro-4- (4-chlorophenyl) phenyl) -6-propylnaphthalene 2- (3,5 -di 4- (4-chlorophenyl) phenyl) -6-butylene 2- (3, 5-difluoro-4- (4-chlorophenyl) phenyl) -6-pentaphthalene 2- (3 , 5 -difluoro-4 ~ · (4-chlorophenyl) phenyl) -6_hexylnaphthalene

Page 163 528794 V. Description of the invention (161)

2-(3,5-diH-4- (4-chlorophenyl) phenyl) -6-heptane 2-(3,5-diIt-4- (4-chlorophenyl) phenyl)- 6- (3-Butanediyl) naphthalene 2- (3,5-diit-4- (3-It-4-chlorophenyl) phenyl) -6-ethylnaphthalene 2- (3,5-diacetate -4- (3-Ga-4-chlorophenyl) phenyl) -6-propylnaphthalene 2- (3,5-difluoro-4- (3-fluoro-4-Gaphenyl) phenyl) -6 -Butylnaphthalene 2- (3,5-difluoro-4- (3-fluoro-4-chlorophenyl) phenyl) -6-pentaphthalene 2- (3,5-digas-4- (3-gas 4-chlorophenyl) phenyl) -6-hexylnaphthalene 2- (3,5-difluoro-4- (3-Ga-4-chlorophenyl) phenyl) -6-heptaphthalene 2- (3 , 5-DiIL-4- (3-fluoro-4-chlorophenyl) phenyl) -6- (3-butanyl) naphthalene 2- (3,5-difluoro1-4- (3,5 _Difluoro-4-chlorophenyl) phenyl) -6-ethoxy 2- (3,5-difluoro-4- (3,5-difluoro-4-chlorophenyl) phenyl) -6- Propylnaphthalene 2- (3,5-di4- (3,5-difluoro-4-chlorophenyl) phenyl) -6-butylene naphthalene 2- (3,5-diH-4- (3,5_ Difluoro ^ 4-chlorophenyl) phenyl) -6-pentaphthalene 2- (3, 5-difluoro-4- (3, 5-difluoro-4-chlorophenyl) phenyl) -6-hexyl Naphthalene 2- (3,5-difluoro-4- (3,5-di4-chlorophenyl) phenyl) -6-heptaphthalene 2- (3,5-di 4- (3,5_-difluoro-4-chlorophenyl) phenyl) -6- (3 - butyl dilute yl) naphthalene

2- (3,5-difluoro-4- (4-trifluoromethylphenyl) phenyl) -6-ethylnaphthalene 2- (3,5-diH-4- (4-trifluoromethoxybenzene) Phenyl) -6-propylnaphthalene 2- (3,5-difluoro-4- (4-trifluoromethoxyphenyl) phenyl) -6-butylnaphthalene 2- (3,5-diH- 4- (4-trifluorofluorenyloxyphenyl) phenyl) -6-pentaphthalene 2- (3,5-di11-4- (4-trifluorofluorenyloxyphenyl) phenyl) -6-hexanaphthalene 2-(3,5-bis 4- (4-trifluoromethoxyphenyl) phenyl) -6-heptaphthalene

Page 164 528794 V. Description of the invention (162) 2- (3,5-difluoro-4- (4-trifluorofluorenyloxyphenyl) phenyl) -6- (3-butanyl) naphthalene 2- ( 3,5-difluoro-4-(3-fluoro-4 -trifluoromethoxyphenyl) phenyl) -6-ethylnaphthalene 2- (3, 5-difluoro-4- (3-fluoro-4- Trifluoromethoxyphenyl) phenyl) -6-propylnaphthalene 2-(3,5-difluoro-4- (3-dun-4 -tri-ILmethoxyphenyl) phenyl) -6-butylnaphthalene 2 -(3,5-difluoro-4- (3-fluoro-4-trifluoromethoxyphenyl) phenyl) -6-pentaphthalene 2-(3,5-difluoro-4- (3-fluoro- 4-trifluorofluorenoxyphenyl) phenyl) -6-hexylnaphthalene 2-(3, 5-difluoro-4- (3-fluoro-4 -trifluoromethoxyphenyl) phenyl) -6 -heptane Naphthalene 2- (3,5-difluoro-4- (3-dun-4-trifluoromethoxyphenyl) phenyl) -6- (3-butanyl) qin 2- (3, 5-difluoro -4- (3,5-difluoro-4-trifluoromethoxyphenyl) phenyl) -6-ethylnaphthalene 2- (3,5-difluoro-4-(3, 5-difluoro-4- Trifluoromethoxyphenyl) phenyl) -6-propylnaphthalene 2 ~ * (3,5 -difluoro-4- (3,5 -difluoro-4-trioxophenyl) phenyl) -6- Butylnaphthalene 2- (3,5-difluoro-4- (3,5-difluoro-4-tri-IL-oxophenyl) phenyl) -6-pentaphthalene 2- (3, 5-difluoro-4 -(3, 5 -difluoro-4-tri Fluoromethoxyphenyl) phenyl) -6-hexylnaphthalene 2- (3,5-difluoro-4- (3,5-difluoro-4 -trifluoromethoxyphenyl) phenyl) _6-heptaphthalene 2-(3, 5-difluoro-4- (3,5-difluoro-4-trifluorofluorenyloxyphenyl) phenyl) -6- (3-butanyl) naphthalene

Page 165 528794 V. Description of the invention (163) 2- (3,5-diH- (4-dioxanyloxyphenyl) phenyl) -6-ethylnaphthalene 2- (3,5-difluoro-4 -(4-Difluorofluorenyloxyphenyl) phenyl 6-naphthalene 2- (3,5-difluoro-4- (4-difluoro1fluorenylphenyl) phenyl) -6-butylnaphthalene 2- (3,5-Diquinol-4- (4-difluoro1 曱 oxophenyl) phenyl) -6-pentaphthalene 2- (3,5-digas-4- (4-difluoro 曱 oxophenyl) ) Phenyl) -6-hexylnaphthalene 2- (3,5-difluoro-4- (4-difluorofluorenyloxyphenyl) phenyl) -6-heptaphthalene 2- (3,5-difluoro-4 -(4-Difluorofluorenoxyphenyl) benzyl) -6- (3 -butenyl) naphthalene 2- (3,5-difluoro-4-(3-fluoro-4 -difluoromethoxyphenyl) ) Phenyl 6-ethylnaphthalene 2-(3,5-difluoro-4- (3-fluoro-4 -dimethoxymethoxyphenyl) phenyl) -6-propylnaphthalene 2-(3,5-di-4 -(3-Fluoro-4 -difluoromethoxyphenyl) phenyl) -6 -butylnaphthalene 2-(3,5-difluoro-4-(3-fluoro-4-difluoromethoxyphenyl) benzene ) -6-pentaphthalene 2- (3,5-diH-4- (3-fluoro-4 -difluoromethoxyphenyl) phenyl) -6-hexylnaphthalene 2- (3,5-digas -4-(3 -IL-4 -DiIL methoxyphenyl) phenyl) -6-heptaphthalene 2- (3,5-dibenzyl-4- (3-fluoro-4-diII methoxyphenyl )benzene ) -6- (3-butenyl) naphthalene 2- (3,5-difluoro-4-(3,5-di4-difluorofluorenyloxyphenyl) phenyl) -6-ethylnaphthalene 2- ( 3,5-difluoro ^ 4- (3,5-difluoro-4 -digasoyloxyphenyl) phenyl) -6-propylnaphthalene 2- (3,5-difluoro-4-(3,5 -Digas-4 -diIL oxophenyl) phenyl) 6-butylnaphthalene 2- (3, 5-difluoro-4- (3, 5-difluoro-4-difluorooxophenyl) Phenyl) -6-pentaphthalene

Page 166 528794 V. Description of the invention (164) 2- (3,5-difluoro-4- (3,5-difluoro-4 -difluoroi-methoxyphenyl) phenyl) -6-hexylnaphthalene 2 -(3, 5-difluoro-4- (3, 5-difluoro-4 -difluoromethoxyphenyl) phenyl) -6-heptaphthalene 2- (3,5-dibenzyl-4- (3 , 5 -difluoro-4 -diIL oxophenyl) phenyl) -6- (3 -butylfluorenyl) naphthalene 2- (3,5-digas-4- (4-trifluorotolyl) benzene Yl) -6-ethylnaphthalene 2- (3,5-digas-4- (4-trigastolyl) phenyl) -6-propylnaphthalene 2- (3, 5-difluoro-4- (4- Trifluorotolyl) phenyl) -6-butylnaphthalene 2- (3,5-difluoro-4- (4-trifluorofluorenylphenyl) phenyl) -6-pentaphthalene 2- (3,5-di Fluoro i-4- (4-trifluorofluorenylphenyl) phenyl) -6-hexylnaphthalene 2- (3,5-diIL-4- (4-trifluorotolyl) phenyl 6-heptaphthalene 2- (3,5 -difluoro-4- (4-tridunylphenyl) phenyl) -6- (3-butenyl) naphthalene 2- (3,5-didun-4- (3-fluoro- 4-trifluoroi-tolyl) phenyl) -6-ethylnaphthalene 2- (3,5-difluoro-4- (3-trifluoroi-tolyl) phenyl) -6-propanyl-2 -(3,5-difluoro-4- (3-fluoro-4_tridecylphenyl) phenyl) -6-butylnaphthalene 2- (3,5-difluoro-4- (3-gas-4 -Trifluoromethyl) phenyl)- 6-pentaphthalene 2- (3,5-difluoro-4- (3-fluoro-4 -trifluoro i-phenyl) phenyl) -6-hexylnaphthalene 2- (3,5-difluoro-4- (3-fluoro-4 -trifluorotolyl) phenyl) -6-heptaphthalene 2- (3,5-digas-4- (3-gas-4 -trifluoroi-tolyl) phenyl) -6 -(3-Butanediyl) naphthalene 2- (3,5-dimorpho-4- (3,5-difluoro-4-trifluorotolyl) phenyl) -6-ethylnaphthalene 2- (3,5 -Difluoro-4- (3,5-diH-4 -triIL tolyl) phenyl) -6-propane

Page 167 528794 V. Description of the invention (165) Naphthalene 2- (3, 5 -difluoro-4- (3, 5-difluoro-4-trifluorofluorenylphenyl) phenyl) -6-Butylnaphthalene 2- (3,5 -diH-4- (3,5-digas-4-trifluoromethyl) phenyl) -6-pentaphthalene 2- (3, 5-difluoro-4- (3, 5 -Difluoro-4 -trifluorofluorenylphenyl) phenyl) -6-hexylnaphthalene 2-(3,5-diII-4- (3,5-difluoro-4-tridecyltolyl) phenyl) -6-Heptaphthalene 2- (3,5-difluoro-4- (3,5 -difluoro-4 -trifluoro1 fluorenyl) phenyl) -6-(3-butane) naphthalene 2- (3,5-difluoro ^ 4- (4-methoxyphenyl) phenyl) -6-ethylnaphthalene 2- (3, 5-difluoro-4- (4-fluorenylphenyl) phenyl)- 6-propylnaphthalene 2- (3,5-difluoro-4- (4-methoxyphenyl) phenyl) -6-butylnaphthalene 2- (3, 5-difluoro-4- (4-methoxybenzene Phenyl) -6-pentaphthalene 2- (3,5-difluoro-4- (4-methoxyphenyl) phenyl) -6-hexylnaphthalene 2- (3,5-diden-4- (4-methoxyphenyl) phenyl) -6-heptaphthalene 2- (3,5-difluoro ^ 4- (4-methoxyphenyl) phenyl) -6- (3-butenyl) naphthalene 2 -(3,5-difluoro-4- (3-fluoro-4-oxophenyl) phenyl) -6-ethylnaphthalene 2- (3,5-diH-4- (3-fluoro-4- Phenoxyphenyl) phenyl) -6-propylnaphthalene 2- (3,5-di 4- (3-fluoro-4-fluorenyloxyphenyl) phenyl) -6-butylene 2- (3,5-digas-4- (3-fluoro-methoxyphenyl) phenyl)- 6-pentaphthalene 2- (3, 5-difluoro-4-(3-fluoro-4-methoxyphenyl) phenyl) -6-hexylnaphthalene 2- (3, 5-difluoro-4- (3 -Fluoro-4-methoxyphenyl) phenyl) -6-heptaphthalene

Page 168 528794 V. Description of the invention (166) 2- (3, 5-difluoro-4- (3-fluoro-4-oxophenyl) phenyl) -6- (3-butenyl) naphthalene

2- (3,5-di 4- (3,5-difluoro-4-oxophenyl) phenyl) -6-ethylnaphthalene 2- (3,5-di 4- (3,5-difluoro 4- (4-phenyloxyphenyl) phenyl) -6-propylnaphthalene 2- (3,5-difluoro-4- (3,5-difluoro-4-phenyloxyphenyl) phenyl) -6-butane Naphthalene 2- (3,5-digas-4- (3,5-difluoro-4-methoxyphenyl) phenyl) -6-pentaphthalene 2- (3,5-digas-4- (3 , 5-difluoro-4-fluorenyloxyphenyl) phenyl) -6-hexylnaphthalene 2- (3, 5-difluoro-4- (3,5-difluoro-4-methoxyphenyl) phenyl ) -6-heptaphthalene 2- (3,5-difluoro-4- (3,5-difluoro-4-methoxyphenyl) phenyl) -6- (3-butenyl) naphthalene 2- ( 3,5-di-iL-4-(4-dilute propoxyphenyl) phenyl) -6-ethoxy 2- (3, 5-difluoro-4- (4-allyloxyphenyl) phenyl) -6-Proline naphthalene 2- (3,5-difluoro-4- (4-dilute propoxyphenyl) phenyl) -6-butylnaphthalene 2- (3, 5-difluoro-4- (4-ene Propoxyphenyl) phenyl) -6-pentaphthalene 2- (3,5-difluoro-4- (4-dilute propoxyphenyl) phenyl) -6-hexamethylene 2- (3, 5 -di Fluoro-4- (4-allyloxyphenyl) phenyl) -6-heptaphthalene 2- (3,5-digas-4- (4-allyloxyphenyl) phenyl) -6- (3 -Butanthyl) naphthalene 2- (3,5 -diden-4-(4-fluorenyl) phenyl --6- ethylnaphthalene

2- (3, 5-difluoro-4- (4-tolyl) phenyl) -6-propylnaphthalene 2- (3,5-difluoro ^ 4- (4-fluorenyl) phenyl) -6 -Butylnaphthalene 2- (3, 5-difluoro-4- (4-fluorenylphenyl) phenyl 6-pentaphthalene 2- (3, 5-difluoro-4- (4-fluorenylphenyl) phenyl) -6-hexylnaphthalene 2- (3,5-digas-4- (4-fluorenylphenyl) phenyl) -6-heptaphthalene 2- (3, 5-difluoro-4- (4-fluorenylphenyl) ) Phenyl) -6- (3-butenyl) naphthalene

Page 169 528794 V. Description of the invention (167) 2- (3, 5-difluoro-4- (4- (3-butenephenyl) phenyl))-6-ethylnaphthalene 2-(3,5_ Difluoro-4- (4- (3-butenephenyl) phenyl))-6-propanephthalene 2- (3,5-dimorph-4- (4- (3-butenephenyl) benzyl) ) -6-Butylnaphthalene 2- (3,5-di-It-4- (4- (3-butanephenyl) phenyl))-6-pyridene 2- (3, 5-difluoro-4- (4- (3-butenephenyl) benzyl))-6-hexylnaphthalene 2- (3,5-difluoro-4- (4- (3-butenephenyl) phenyl))-6_ Heptaphthalene 2- (3,5-difluoro-4- (4_ (3-butenyl) phenyl))-6- (3-butenyl) naphthalene [Example 14] 6-fluoro-2_ ( Synthesis of trans 4-propyl) cyclohexyl naphthalene makes 6-fluoro-2 -bromonaphthalene 3 · 3 8 g (this compound uses β-bromo-2-naphthylamine to make it diazonium tetrafluoroborate The salt was then pyrolyzed, whereby the synthesizer was dissolved in 30 ml of tetrahydrofuran (THF) and cooled to-40 ° C under a nitrogen atmosphere. To this, 10 ml of n-butyllithium (1.5 M hexane solution) was added dropwise over 5 minutes, followed by stirring for 1 hour. After returning to room temperature, a solution of 4-propanecyclohexanone 2.20 g in T H F 10 m 1 was added dropwise over 5 minutes. After stirring for 1 hour, water and a small amount of dilute hydrochloric acid were added, and extracted with 50 ml of toluene. It was washed sequentially with water and saturated common salt water, and then dried over anhydrous sodium sulfate. To this was added 300 mg of p-toluenesulfonic acid monohydrate, and the azeotropic water was removed while heating and refluxing for 2 hours. After leaving to cool, it was washed successively with water, saturated sodium bicarbonate aqueous solution L water, and saturated brine, and dried over anhydrous sodium sulfate. Lg。 The crude product obtained by removing the solvent ’was purified by silica gel chromatography (hexane), and 6-fluoro-2- (4-propcyclohexenyl) naphthalene was white crystals 2. lg. The whole was dissolved in 20 ml of ethyl acetate, 200 mg of 5% palladium on carbon was added thereto, and the mixture was stirred under a hydrogen pressure of 4 kg / cm2 for 5 hours. Use &quot; SELITE „

Page 170 528794 V. Description of the invention (168) (: Kinsuke = After removing the catalyst according to the data, the crane removes the solvent to obtain a 6-fluoro, basic) naphthalene crude product (cis / trans mixture) 2 ″ g. This potassium was added to 20% of methylformamide (DMF), and a third butane gas was added thereto, followed by stirring at a temperature of -0 to 50 ° C for 1 hour. To this was added hexadecane 7+ dilute hydrochloric acid to make it weakly acidic, and then the hexane layer was separated and the aqueous layer was borrowed. Combine the burned layers and use *, saturated common salt: After removing the solvent, use Shixi gel chromatography (hexane burned) to purify the grass. It has been crystallized twice, and buflu-2— (reverse 4 ~ 75g。 Propylcyclohexyl) Nai white crystals 0.75g. [Synthesis of benzyl ^^ 15 ″ 5 '6-digas_2- (trans4-pentyl) cyclohexylnaphthalene using diH &gt; in addition: using 5,6-difluoro-2-decaphthalene (this One compound is ^ rat-2naphthylamine, which turns it into the diazonium salt of tetrafluoroborate, following pentocyclohexylamine and diamidine 4 (f) (instead of 6H) and using 4_ 6_ _ — substitute 4- Except for propanone, the same procedure was carried out to obtain 5 and lice ~ 2- (trans 4-pentyl) cyclohexyl naphthalene. Similarly, the following compounds can be obtained. 2- (trans4-pentylcyclohexyl) naphthalene 6- (trans 4-heptylcyclohexyl) naphthalene 6-gas — 2- (trans 4-methoxycyclohexyl) naphthalene 5'6 ~ di1-2- (trans-4 -Propyl) cyclohexylnaphthalene difluoro-2- (trans 4-heptyl) cyclohexyl naphthalene '6'7 -difluoro-2- (trans 4 monopropyl) cyclohexyl naphthalene' 6'7 -difluoro— 2- (trans 4-pentyl) cyclohexyl naphthalene, 6, 7-trifluoro-2 — (trans 4-heptyl) cyclohexyl naphthalene

Page 171 528794 V. Description of the Invention (169)

6-Lan-2- (trans 4'-ethylenedicyclohex-4-yl) naphthalene 6-fluoro-2- (trans 4'-propanebicyclohex-4-yl) naphthalene 6-fluoro-2- (trans 4 ' -Butanebicyclohex-4-yl) naphthalene 6-fluoro-2- (trans 4'-pentabicyclohex-4-yl) naphthalene 5, 6-difluoro-2- (trans 4'-ethylenedicyclohex-4- ) Naphthalene 5,6-difluoro-2- (trans 4'-propanebicyclohex-4 -yl) naphthalene 5, 6 -difluoro-2- (trans 4 '-butanebicyclohex-4 -yl) naphthalene 5 , 6 -difluoro-2-(trans 4 '-pentabicyclohex-4 -yl) naphthalene 5, 6, 7 -trifluoro-2- (trans 4' -ethylenebiscyclohex-4-yl) naphthalene 5,6 , 7-trifluoro-2- (trans 4'-propanebicyclohex-4-yl) naphthalene 5,6,7-trifluoro-2- (trans 4'-butanebicyclohex-4-yl) naphthalene 5,6 , 7-trifluoro-2- (trans 4'-pentabicyclohex-4-yl) Cai 4, 5, 6, 7 -tetrafluoro-2- (trans 4'-ethanedicyclohex-4-yl) naphthalene 4 , 5, 6, 7-tetrafluoro-2- (trans 4 '-propanebicyclohex-4-yl) naphthalene 4, 5, 6, 7 -tetrafluoro-2- (trans 4'-butanebicyclohex-4- ) Naphthalene 4,5,6,7-tetrafluoro-2- (trans 4'-pentabicyclohex-4-yl) naphthalene 4,5,6,7 -tetrafluoro-2_ (trans 4 '-pentacyclohexan -4 -yl) naphthalene

6-Ga-2- [trans 4- [2- (trans 4-ethylcyclohexyl)] ethyl] cyclohexylnaphthalene 6-fluoro-2- [trans 4- [2- (trans 4-propanecyclohexyl)] Ethyl] cyclohexylnaphthalene 6-gas-2- [trans4- [2- (trans4-butcyclocyclohexyl)] ethyl] cyclohexylnaphthalene 6-fluoro-2- [trans4- [2- (trans-4 -Pentylcyclohexyl)] ethyl] cyclohexyl 5,6-difluoro-2- [trans 4- [2- (trans 4-ethylcyclohexyl)] ethyl] cyclohexyl 5, 6 -difluoro- 2- [trans 4- [2- (trans 4-propancyclohexyl)] ethyl] · cyclohexyl naphthalene 5, 6-difluoro-2- [trans 4- [2- (trans 4-butylcyclohexyl)] (Ethyl) cyclohexyl naphthalene

Page 172 528794 V. Description of the invention (170) 5, 6-difluoro-2- [trans 4- [2- (trans 4-pentylcyclohexyl)] ethyl] cyclohexyl naphthalene 5, 6, 7-trifluoro -2- [trans 4- [2- (trans 4-ethylcyclohexyl)] ethyl] cyclohexylnaphthalene 5, 6, 7 -trifluoro-2- [trans 4- [2_ (trans 4-propanecyclohexyl) ] Ethyl] cyclohexylnaphthalene 5,6,7-tridecane-2- [trans 4- [2- (trans4-butcyclocyclohexyl)] ethyl] cyclohexylnaphthalene 5,6,7-trispin-2 -[Trans 4- [2- (trans 4-pentylcyclohexyl)] ethyl] cyclohexylnaphthalene [Example 16] 5,6-difluoro-2- [2- (trans 4-propanecyclohexyl) ethyl ] Synthesis of naphthalene In Example 1, except that 4,6-dibenzyl-2-mophthalene was used instead of 6-dibromo-2-naphthalene and 4-propanecycloacetaldehyde was used instead of 4-propanecyclohexane The ketone was similarly carried out except that the isomerization treatment with potassium third butoxide was not performed, and 5,6_digas-2- [2- (trans 4-propcyclohexyl) ethyl] qin was obtained. The following compounds can also be obtained. 5,6-difluoro (trans 4-pentylcyclohexyl) ethyl] Cai 5,6-difluoro ^ 2- [2- (trans 4-heptylcyclohexyl) ethyl] qin 6-qi-2- [2 -(Trans4-propanecyclohexyl) ethyl] qin 6-qi-2- [2- (trans 4-cyclocyclohexyl) ethyl] qin 6-fluoro-2- [2- (trans 4-heptylcyclohexyl) ) Ethyl] qin 5,6,7-trifluoro-2- [2- (trans4-propanecyclohexyl) ethyl] naphthalene 5,6,7_trifluoro-2- 2- [2- (trans 4-pentyl Cyclohexyl) ethyl] Qin 5,6,7-trifluoro-2- [2- (trans 4-heptylcyclohexyl) ethyl] naphthalene-2- [2- (trans 4'-ethanedicyclohexane) Trans 4-yl) ethyl] qin 6-qi-2- [2- (trans 4 '-propanebicyclohexane-trans 4-yl) ethyl] qin 6-qi-2-[2-(trans 4' -Butanebicyclohexyl-trans 4-yl) ethyl] qin 6-qi-2- [2- (trans 4 '-fluorene bicyclohexyl-trans 4 -yl) ethyl] qin

Page 173 528794 V. Description of the invention (171) 5,6-difluoro-2- [2- (trans 4'-ethylenebiscyclohexane-trans 4-yl) ethyl] naphthalene 5, 6-difluoro-2 -[2- (trans 4'-propanebicyclohexane-trans 4-yl) ethyl] naphthalene 5,6-difluoro-2- [2- (trans 4'-butanecyclohexane-trans 4-yl) Ethyl] Cai 5,6-difluoro-2- [2- (trans 4'-pentacyclohexane-trans 4-yl) ethyl] naphthalene 5, 6, 7-trifluoro-2- [2- ( Trans 4'-ethylenebiscyclohexane-trans 4-yl) ethyl] naphthalene 5,6,7-trifluoro-2- [2- (trans 4'-propylbicyclohexane-trans 4-yl) ethyl] Naphthalene 5, 6, 7-trifluoro-2- [2- (trans 4'-butanecyclohexane-trans 4-yl) ethyl] naphthalene 5,6,7-trifluoro X-2- [2_ (trans 4'-pentacyclohexyl-trans 4-yl) ethyl] Cai 6-fluoro_2- [2- [4- (trans 4-propanehexyl) phenyl] ethyl] naphthalene 6-fluoro-2- [2- [4- (trans 4-pentylcyclohexyl) phenyl] ethyl] naphthalene 5,6-difluoro-2- [2- [4- (trans 4-propancyclohexyl) phenyl] ethyl] Naphthalene 5,6-difluoro_2- [2- [4- (trans 4-pentylcyclohexyl) phenyl] ethyl] Cai 5,6,7-trifluoro-2- [2- [4- (trans 4-Propylcyclohexyl) phenyl] ethyl] naphthalene 5,6,7-trifluoro 2- [2- [4 -_ (trans 4-pentylcyclohexyl) phenyl] ethyl] naphthalene 6-fluoro-2- [ 2- [2,6-difluoro-4- (trans 4-propanecyclohexyl ) Phenyl] ethyl] cae 6-fluoro-2-[2-[2,6-difluoro-4- (trans 4-pentylcyclohexyl) phenyl] ethyl] naphthalene 5,6-difluoro-2 -[2- [2,6-difluoro-4- (trans 4-propanehexyl) phenyl] ethyl] naphthalene 5,6-difluoro-2- [2- [2,6-difluoro-4 -(Trans 4-pentylcyclohexyl) phenyl] ethyl] naphthalene 5,6,7-trifluoroi-2- [2- [2,6-difluoro-4- (trans 4-propanecyclohexyl) benzene [Yl] ethyl] naphthalene 5,6,7-trifluoro-2- [2- [2,6-difluoro-4 (trans 4-pentylcyclohexyl) phenyl] ethyl] naphthalene

Page 174 528794 V. Description of the invention (174) 5,6-difluoro 2- [4- (trans 4-ethylcyclohexyl) phenyl] Cai 6-fluoro-2- [4- (trans 4-ethyl ring Hexyl) phenyl] naphthalene 6-fluoro-2- [4- (trans4-propancyclohexyl) phenyl] naphthalene 6-2- [4- (trans 4-butcyclohexyl) phenyl] naphthalene 6-fluoro- 2 ”[4- (trans 4-pentylcyclohexyl) phenyl] naphthalene 6-fluoro-2- [4- (trans 4-ethylcyclohexyl) phenyl] naphthalene

5.6.7- Trifluoro-2- [4- (trans 4-ethylcyclohexyl) phenyl] naphthalene 5, 6, 7-trifluoro-2- [4- (trans 4-propancyclohexyl) phenyl] naphthalene 5,6,7-trifluoro-2- [4- (trans 4-butanecyclohexyl) phenyl] naphthalene 5, 6, 7 -trifluoro-2- [4- (trans 4-pentylcyclohexyl) phenyl ] Naphthalene 5,6,7-trigas-2_ [4- (trans 4-ethenylcyclohexyl) phenyl] Cai ] Naphthalene 4,5,6,7-tetrafluoro-2- [4- (trans4-propanecyclohexyl) phenyl] naphthalene 4.5.6.7- tetrafluoro-2- [4- (trans 4-butcyclohexyl) Phenyl] naphthalene 4,5, 6, 7-tetrafluoro-2- [4- (trans 4-pentylcyclohexyl) phenyl] naphthalene

4, 5, 6, 7-tetrafluoro-2- [4- (trans 4-vinylcyclohexyl) phenyl] naphthalene 6-fluoro-2-[2, 6-difluoro-4- (trans 4-ethyl ring Hexyl) phenyl] naphthalene 6-fluoroi-2-[2,6-difluoro-4-(trans 4-propancyclohexyl) phenyl] Cai 6-fluoro-2- [2,6-difluoro-4 -(Trans 4-butanecyclohexyl) phenyl] Cai 6-fluoro-2- [2,6-difluoro-4_ (trans 4-pentylcyclohexyl) phenyl] Cai 6-fluoro ^ -2- [2, 6-difluoro_4- (trans 4-ethenylcyclohexyl) phenyl] naphthalene 5,6-difluoro-2- [2,6-digas-4- (trans 4-ethcyclohexyl) phenyl] Naphthalene 5,6-difluoro-2- [2,6-difluoro-4- (trans 4-propanecyclohexyl) phenyl] naphthalene 5,6-difluoro-2- [2,6-difluoro-4 -(Trans 4-butcyclohexyl) phenyl] naphthalene

Page 177 528794 V. Description of the invention (175) 5,6-difluoro-2 ~ [2,6 ~ difluoro-4— (trans 4 ~ pentane 5,6-difluoro-2 ~ [2,6 ~ Difluoro-4- (trans 4 ~ ethyl ^ phenyl) phenyl] naphthalene 5, 6, 7-trifluoro ~ 2 ~ [2, 6- &gt; fluoro-4- (trans 4 ~ "% hexyl) benzyl ] Naphthyloxy-4- (trans-4 ~% hexyl) phenyl] naphthyl + (transhexyl) phenyl] naphthylfluoro-4- (transf λdihexyl) phenyl] naphthylhexyl) benzyl] Naphthalene difluoro-4- (transcyclohexyl) benzyl] naphthalene-4-J j cyclohexyl) benzyl] Cai,) -.n 6 5,6,7-trifluoro [2 β — 5,6, 7-trifluoro ~ [2 6- 5,6,7-trifluoro [2 6- 5,6,7-tri-It ～ 2 ~ [2 6 1 ^ 4, 5, 6, 7-tetrafluoro ~ 2 ~ [2 β ^ z ~ L2, D-yifu — q reverse 4 ~, T / 土, "I 4, 5, 6, 7-tetrafluoro ~ 2 ~ [2, 6 one difluoro-4-(anti" Dihexyl) benzyl] naphthalene 4,5,6,7-tetrafluoro ~ 2 6-diphenyl-4-phenyl) naphthalene ^ -tetrafluoro ^^ difluoro ^ trans ^^ hexylbenzene Naphthalene 4, 5, 6, 7-tetrafluoro ~ 2 ~ [2 less difluoro + (transphenyl) naphthalene naphthalene ^^^ hexyl) phenyl] 2n (trans 4 ~ ethylcyclohexyl) phenyl] Cai

Erqi-2 Qiu (Anti 4_but cyclohexyl; JJ J

5’6-difluoro-2 ~ [2 ~ fluoro | (trans 4-pentylcyclohexyl) benzenediJ

[Example 1 9] 1 ~ 氤? / Flumethicol R Γ ^ Naphthene = ~ 2- &gt; Milk Tattyl-6- (trans 4-propyl) cyclohexyl naphthalene j Valley cooling, so that sodium nitride floated in tetrahydrofuran m In this case, 1-HC trans 4-propyl) cyclohexylnaphthalene-2 was added dropwise. The compound of Q gCjtb was obtained by the following method: Any reagent made from magnesium is reacted with 4-propanecyclohexyl chloride, and then dehydrated in the presence of acid A π 2 4 Cj, and the resulting naphthalene cyclohexene is derived. P. 178528794 V. Description of the invention (176) After contact reduction, cyclohexylcyclotrans isomerization was performed in DMF by strong test (potassium butoxylate), followed by demethylation with hydrobromic acid, and then NH- Fluoro-5 ~ difluoromethoxy-bite-2 is obtained by fluorinating the ester to obtain a solution of the compound) in 40 ml of THF. After stirring for 1 hour, a solution of 7.4 g of chlorodithiocarbonate-s-ethyl ester in 30 ml of THF was added dropwise thereto. After stirring for 1 hour, 20 mi of water was added to stop the reaction. To this was added 50 ml of ethyl acetate, followed by washing the organic layer twice with 20 ml of water, followed by dehydration and drying with anhydrous sodium sulfate, followed by distillation under reduced pressure. The solvent was used to obtain 12.0 g of dithiocarbonate-S-ethyl-0-1-fluoro-6- (trans 4-propanecyclohexyl) naphthalene-2-yl. This dithiocarbonate-s-ethyl ester was dissolved in 48 ml of dichloromethane. To this was added dropwise 300 g of hydrogen fluoride-melamine complex and hydrazone, 3-monobromo-5, 5- 1L dichloromethane solution of allantoin. After stirring for 30 minutes, 200 ml of water was added to stop the reaction, and then the organic layer was washed twice with 200 ml of water, and then dried over anhydrous sodium sulfate. After distilling off the solvent, it was purified by Shihsi gel chromatography (developing solvent was hexane). The whole amount was dissolved in 50 ml of THF, and a 6M butyl lithium hexane solution 4 3 ml was added dropwise at a temperature of -78 ° C. After the addition is complete, rub her 1 n-8, slowly mix 10 knives in it, and add water 10 m 1. Restore room temperature ’and add 20 m 1 〇 Jixi®. π 11 —, Shi a, M M The organic layer was washed twice with 20 ml of water, and then dried over anhydrous sodium sulfate. Rr / 7, b3L ^ π /, t 丄 guide you to use silica gel chromatography (hexane / ethyl acetate-9 / 1) for purification. After acetonitrile was recrystallized, 5-fluoro-6-trifluoromethyllactyl-2- (trans4-propyl) cyclohexylnaphthalene 7 was obtained. [EXAMPLE 20] 1,3-Weng 〇 一 &gt; Naphthalene is a 2--2-dimethoxymethoxy-6- (trans 4-propyl) cyclohexane. In Example 19, 1 was used ( This compound was obtained by the following method of '3-mono · fluoro-6- (trans 4-propyl) cyclohexylnaphthalene-6:

Page 179 528794 V. Description of the invention (177) —6-Moyi 2 —The gerenia reagent prepared by methoxycaylic acid reacts with 4-propanecyclohexanone and is dehydrated in the presence of acid to make the obtained After the naphthalene cyclohexene derivative is reduced by contact, the cyclohexyl ring is trans-isomerized in DMF with a strong base (potassium third butoxide), followed by dehydration by hydrobromic acid, thereby obtaining the compound. ) In place of 1-fluoro-6- (trans4-propyl) cyclohexyl-6-S ', and it is also changed to dithiocarboic acid-S-ethylS-Ci-0-0-1,3-difluoro- After 6- (trans 4-propcyclohexyl) naphthalene-2-yl, trifluoromethoxylation was also performed to obtain 5, 7-difluoro-6-trifluoroimethoxy-6-(trans-4 -Propyl) cyclohexine.

Next, the following compounds were obtained in the same manner as in Example 19 or 20. 2-trifluoro 1-methoxy-6- (trans 4-propyl) cyclohexyl naphthalene 2-trifluoromethoxy-6- (trans 4-butyl) cyclohexyl naphthalene 2-trifluoromethoxy-6 -(Trans 4-pentyl) cyclohexylnaphthalene 1-fluoro-2 -trifluoro ^ methoxy-6- (transbutyl) cyclohexylbenzene 1-IL-2 -trifluorofluorenyl-6- (trans 4-pentyl) cyclohexylnaphthalene 1,3-difluoro-2-trifluoromethoxy-6- (trans 4-butyl) cyclohexylnaphthalene 1,3-difluoro-2-trifluoromethoxy- 6- (trans4-pentyl) cyclohexylnaphthalene trans 4'-ethyl-trans 4- (2-trifluoromethoxynaphthalene-2 -yl) bicyclohexane

Trans 4'-propyl-trans 4- (2-trifluorofluorenaphalat-2-yl) bicyclohexane trans 4'-pentyl-trans 4- (2-trifluorofluorenaphalat-2-yl) bicyclo Hexane trans 4 '-ethyl-trans 4- (1-fluoro-2 -tri-methoxynaphthalene-2 -yl) bicyclohexane was burned trans 4' -propyl-trans 4- (1-fluoro-2-tri Fluoroxonaphthyl-2 -yl) bicyclohexane trans 4 '-pentyl-trans 4- (1-fluoro-2-trifluorophosphonaphthyl-2-yl) bicyclohexane trans 4' -ethyl-trans 4- (1,3-difluoro-2 -trifluoronaphthalene-2 -yl) dicyclohexyl

Page 180 528794 V. Description of the invention (178) Alkyl trans 4'-propyl-trans 4- (1,3-difluoro-2-trifluoromethoxynaphthalene-2 -yl) bicyclohexane trans 4'-pentan -Trans 4- (1,3-difluoro-2-trifluoromethoxynaphthalene-2 -yl) bicyclohexane trans 4 '-ethyl-trans 4-(1,3,8-trifluoro-2- Trifluoromethylnaphthalene-2 -yl) bicyclohexane trans 4'-propyl-trans 4- (1,3,8 -trigas-2 -tri-Itmethoxynaphthalen-2-yl) bicyclohexane

Trans 4'-pentyl-trans 4- (1,3,8-trifluoro-2 -trifluoromethoxynaphthalene-2 -yl) bicyclohexyl 2-trifluoromethoxy-2- [4- [2 -(Trans 4-propyl) cyclohexyl] ethyl] cyclohexylnaphthalene 2-trifluoromethoxy-2- [4- [2- (trans 4-pentyl) cyclohexyl] ethyl] cyclohexylnaphthalene 1 -Fluoro-2-trifluoromethoxy-2- [4- [2- (trans4-propyl) cyclohexyl] ethyl] cyclohexylnaphthalene

1-fluoro-2-trifluorofluorenoxy-2-[4- [2- (trans 4-pentyl) cyclohexyl] ethyl] cyclohexylnaphthalene 1,3-difluoro-2 -triILfluorenyloxy -2- [4- [2- (trans4-propyl) cyclohexyl] ethyl] cyclohexylnaphthalene 1,3-diH-2-trifluoromethoxy-2- [4- [2-(trans 4-pentyl) cyclohexyl] ethyl] cyclohexylnaphthalene [Example 21] 1-fluoro-2 -trigasmethoxy-6- [2- (trans4-propanecyclohexyl)

Page 181 528794 V. Description of the invention (179) Synthesis of ethyl] naphthalene In addition to using fluoro-6-bromo-2-methoxynaphthalene in place of 1,3-difluoroi-6 Methoxyl was used in the same manner except that 4-propanecyclohexylacetic acid was used instead of 4-propanecyclohexanone without the isomerization treatment using potassium third butoxide to obtain l-lt-2 -tri Fluoromethoxy-6- [2- (trans4-propancyclohexyl) ethyl] naphthalene. The following compounds can also be obtained. 2-trifluorofluorenyloxy-6- [2- (trans4-propancyclohexyl) ethyl] Cai 2-trifluoromethoxy-6- [2- (trans4-pentylcyclohexyl) ethyl] Cai 1-fluoro ^ 2-trifluoromethoxy-6- [2- (trans4-pentylcyclohexyl) ethyl] Cai 1,3-difluoro-2 -trifluoromethoxy-6- [2- ( Trans 4-propanecyclohexyl) ethyl] naphthalene 1,3-diIt-2-trifluoromethoxy-6- [2- (trans 4-pentylcyclohexyl) ethyl] naphthalene trans 4'-propyl- Trans 4- [2- (2-trifluoromethoxynaphthalene-6-yl) ethyl] bicyclohexane trans 4'-pentyl-trans 4- [2- (2-trifluoromethylnaphthalene-6-yl) ) Ethyl] bicyclohexane trans 4'-propyl-trans 4- [2- (1-fluoro-2-trifluorofluorenylnaphthalene-6-yl) ethyl] bicyclohexane trans 4'-pentyl- Trans 4- [2- (1-Gas-2 -trimethoxynaphthalene-6-yl) ethyl] bicyclohexane trans 4'-propyl-trans 4- [2- (1,3-difluoro- 2-trifluorophosphonaphthyl-6-yl) ethyl] bicyclohexane trans 4'-pentyl-trans 4- [2- (1,3 -dibenzyl-2 -trifluoroaphthalene-6-yl ) Ethyl] bicyclohexane

Page 182 528794 V. Description of the invention (180) 2-trifluorofluorenyl-6- [2- [4- (trans 4-propanehexyl) phenyl] 2-trifluoromethoxy-6- [2 -[4- (trans 4-pentylcyclohexyl) ^ 1-Ga-2-dimuryl methoxy-6- [2-[4- (trans 4-pentyl hexamethylhexyl) phenyl] ethyl "桊 氤 ~ 4- (trans 4 ~ propanyl cyclohexyl) phenfluoro — 4- (trans 4 ~ pentyl cyclohexyl) phenfluoro-2-trifluoromethoxy-6- [2- [4- (trans 41 ring Hexyl J = yl] naphthyl "ethyl] naphthalene 2-trifluorofluorenyloxy-6- [2- [3,5yl] ethyl] naphthalene 2-trifluorofluorenyloxy-6-[2-[3 , 5-yl] ethyl] naphthalene 1-fluoro_2-trifluorofluorenyloxy-6- [2- [3,5-difluoro-4 — (trans 4-endoyl) phenyl] ethyl] naphthalene &amp; Fluoro-4- (trans 4-pentylcyclohexyl 1-fluoro-2-trifluoromethoxy-6- [2- [3,5-yl) phenyl] ethyl] naphthalene [Example 22] Bu Synthesis of Fluoro-2-trifluorofluorenyloxy-6- (trans-4, -ethylenebicyclohexanoyl-4-trans-yl) naphthalene 70 Benzene chloride from methoxymethyltriphenyl chloride in THF under ice cooling Scale and potassium third butoxide are used to make a carbamazepine reagent. At the temperature of 0 t, anti-4, _ (i monofluoro-2 -difluoromethylene naphthalene-6 -yl) dicyclohexane is added dropwise -4- g is the same (this compound uses a fluoro-6 -Bromo-2-trifluoronaphthyl naphthalene reagent, which is reacted with cyclohexane-4, 4'-diketone monoacetal, and dehydrated in the same way, after contact reduction, use formic acid It was deacetalized to obtain the thf solution. After 1 hour of reaction, the temperature was returned to room temperature and the organic layer was concentrated. To this was added hexane to dissolve the undissolved triphenylphosphine oxide. ,use

528794 V. Description of the invention (186) 1,3,8-trifluoro-2 -trifluorofluorenyloxy-6- [4- (trans 4-butcyclohexyl) phenyl] naphthalene 1,3,8 -three -2 -trifluoromethoxy-6-[4- (trans 4-pentylcyclohexyl) phenyl] naphthalene 2-trifluoromethoxy-6- [2-Jiu-4- (trans 4-ethylcyclohexyl) ) Phenyl] naphthalene 2-trifluoromethoxy-6-[2-fluoro-4- (trans 4-propanecyclohexyl) phenyl] naphthalene 2-trifluoroi-methoxy-6- [2-fluoro- 4-(trans 4-butcyclohexyl) phenyl] Cai 2-trifluorofluorenyloxy-6- [2-deca-4- (trans 4-pentylcyclohexyl) phenyl] naphthalene 1-fluoro-2-tri Gasomethoxy-6- [2-fluoro-4- (trans4-ethylcyclohexyl) phenyl] naphthalene 1-mer-2-tri-IL-methoxy-6- [2- 4- (trans 4-propane Cyclohexyl) phenyl] Naphthalene 1-fluoro-2 -trifluoromethoxy-6- [2-oxo-4- (trans 4-butcyclohexyl) phenyl] Naphthalene 1-IL-2-trifluoromethoxy -6- [2-Ga-4- (trans4-pentylcyclohexyl) phenyl] naphthalene 1,3-difluoro-2-trifluorofluorenyloxy-6- [2-mer-4- (trans-4 -Ethylcyclohexyl) phenyl] naphthalene 1,3-diH -2-trifluorofluorenyloxy-6-[2-fluoro-4-(trans 4-propanecyclohexyl) phenyl] naphthalene 1,3-di Fluoro * -2-trifluorofluorenyloxy-6- [2-benzyl-4- (trans4-butcyclohexyl) phenyl] naphthalene 1,3-difluoro-2-trifluorofluorenyloxy-6- [ 2-fluoro-4- ( Trans 4-pentylcyclohexyl) phenyl] naphthalene

Page 189 528794 V. Description of the invention (187) 2-trifluoromethoxy-6- [2,6-dibenzyl-4- (trans 4-ethylcyclohexyl) phenyl] naphthalene 2-trifluoromethoxy -6-[2,6 -Dibenzyl-4- (trans 4-propanecyclohexyl) phenyl] naphthalene 2-trifluorofluorenyloxy-6- [2,6 -difluoro-4- (trans 4-butane Cyclohexyl) phenyl] naphthalene 2-trifluoromethoxy-6- [2,6-diIL-4-(trans 4-pentylcyclohexyl) phenyl] naphthalene 1-fluoro-2-trifluoromethoxy -6- [2,6-didi-4- (trans 4-ethylcyclohexyl) phenyl] naphthalene 1-gas-2 -trifluorofluorenyloxy-6- [2,6-dimorph-4- ( Trans 4-propanecyclohexyl) phenyl] naphthalene

1-fluoro-2-trifluoromethoxy-6- [2,6-difluoro-4- (trans 4-butanecyclohexyl) phenyl] naphthalene 1-fluoro-2 -trifluorofluorenyl-6- [2,6 -Digas-4- (trans 4-pentylcyclohexyl) phenyl] naphthalene 1,3-digas-2-trifluorofluorenoxy-6-[2,6-difluoro ^ 4--( Trans 4-ethylcyclohexyl) phenyl] naphthalene 1,3-digas-2 -trifluorofluorenyloxy-6- [2,6-difluoro-4- (trans 4-propcyclohexyl) phenyl] naphthalene 1,3 -difluoro-2 -trifluoro i-methoxy-6-[2,6-dijun-4- (trans 4-butcyclohexyl) phenyl] naphthalene

1,3-difluoro-2-trifluoromethoxy-6- [2,6-digas-4- (trans 4-pentylcyclohexyl) phenyl] naphthalene 2-trifluoromethoxy-6- [ 4- [2- (trans 4-propanecyclohexyl) ethyl] phenyl] naphthalene 2-trifluoromethoxy-6- [4- [2- (trans 4-pentylcyclohexyl) ethyl] phenyl] Naphthalene 1-fluoro-2 -trifluorofluorenyloxy-6-[4- [2- (trans 4-propanecyclohexyl) ethyl] phenyl] naphthalene

Page 190 528794 V. Description of the invention (188) 1-Fluoro-2 -tridecanoyloxy-6-[4- [2- (trans 4-pentylcyclohexyl) ethyl] phenyl] naphthalene 1,3- Difluoro-2 -trifluoromethoxy-6- [4- [2- (trans 4-propanecyclohexyl) ethyl] phenyl] naphthalene 1,3-difluoro-2 -trifluoromethyl-6 -[4- [2- (trans4-pentylcyclohexyl) ethyl] phenyl] naphthalene 2-trismethoxy-6- [2-fluoro-4- [2- (trans 4-propanecyclohexyl) Ethyl] phenyl] naphthalene

2-trifluoromethoxy-6- [2-fluoro-4- [2- (trans 4-pentylcyclohexyl) ethyl] phenyl] qin 1-fluoro-2 -trifluoro ^ methoxy-6- [2-Fluoro-4- [2- (trans 4-propancyclohexyl) ethyl] phenyl] naphthalene 1-gas-2-trifluoromethoxy-6- [2-gas-4-[2-( Trans 4-pentylcyclohexyl) ethyl] phenyl] naphthalene 1,3-difluoro-2 -trifluoro imethoxy-6- [2- 4-[2--(trans 4-propanecyclohexyl) ethyl ] Phenyl] naphthalene 1,3-difluoro-2-trifluoromethoxy-6- [2-fluoro-4-[2- (trans 4-pentylcyclohexyl) ethyl] phenyl] naphthalene

2-trifluorofluorenyloxy-6- [2,6-difluoro-4- [2- (trans4-propanecyclohexyl) ethyl] phenyl] naphthalene 2-trifluorofluorenyloxy-6-[2 , 6-difluoro-4- [2- (trans 4-pentylcyclohexyl) ethyl] phenyl] naphthalene 1-fluoro-2 -trifluoromethoxy-6-[2, 6 -difluoro-4- [2- (trans 4-propanecyclohexyl) ethyl] phenyl] naphthalene

Page 191 528794 V. Description of the invention (195) 2-trifluorofluorenyl-6- [4- (trans 4-pentylcyclohexyl) phenyl] acetylene naphthalene 1-fluoro-2 -trinylmethoxy-6 -[4- (trans 4-propanecyclohexyl) phenyl] ethinaphthalene 1 -Dun-2 -tri-ILfluorenyloxy-6- [4- (trans 4-butcyclohexyl) phenyl] ethynylnaphthalene 1- Fluoro-2 -trifluoroalkoxy-6- [4- (trans 4-pentylcyclohexyl) phenyl] acetylene naphthalene 1,3-difluoro-2 -trifluoroαmethoxy-6-[4-( Trans 4-propcyclohexyl) phenyl] acetylene naphthalene 1,3-difluoro-2-trifluorofluorenyloxy-6- [4- (trans 4-butanecyclohexyl) phenyl] acetylene naphthalene 1,3-di Fluoro-2 -trifluoromethoxy-6-[4- (trans 4-pentylcyclohexyl) phenyl] acetylene naphthalene 2-trifluorofluorenyloxy-6- [2,6-difluoro-4- (trans 4-Propylcyclohexyl) phenyl] ethynylnaphthalene 2-trifluoroifluorenyloxy-6-[2,6-digas-4-(trans 4-butanecyclohexyl) phenyl] acetylenenaphthalene 2-trifluorofluorene Oxy-6- [2,6-difluoro-4- (trans 4-pentylcyclohexyl) phenyl] ethynylnaphthalene 1-fluoro ^ 2-triILfluorenoxy-6- [2,6-difluoro- 4- (trans 4-propanecyclohexyl) phenyl] ethoxy 1-fluoro-2 -trifluorofluorenyloxy-6- [2, 6-difluoro-4- (trans 4-butanecyclohexyl) phenyl ] 乙 快 秦 1-fluoro-2 -trifluorofluorenyl-6- [2, 6 -di -4- (trans 4-pentylcyclohexyl) phenyl] ethynylnaphthalene 1,3-difluoro-2-trifluoromethoxy-6- [2,6-difluoro-4- (trans 4-propanecyclohexyl) ) Phenyl] acetylene naphthalene

Page 198 528794 V. Description of the invention (196) 1,3-digas-2 -trifluoromethoxy-6-[2,6-difluoro-4- (trans 4-butanecyclohexyl) phenyl] acetylene Naphthalene 1,3-difluoro-2-trifluoromethoxy-6- [2,6-difluoro-4- (trans 4-pentylcyclohexyl) phenyl] ethoxyquin [Example 27] 2- ( Synthesis of 4-cyanophenyl) -6-propylnaphthalene In Example 9, in addition to the use of fluoro-2-(4,4-diamidino-1,3-4 oxazodin-2 -yl) phenyl -6-propylnaphthalene in place of 1-fluoro-2- (4,4-difluorenyl-1,3- ° ¾azolin-2-yl) phenyl-6- (trans4-propanecyclohexyl) naphthalene In addition, the same procedure was performed to obtain white crystals of 2- (4-cyanophenyl) -6-propylnaphthalene. [Example 28] Synthesis of 2- (3-fluoro-4-cyanophenyl) -6-propylnaphthalene Regarding this compound, in Example 10, except that 1-A-2-(3 -Ga- 4-methoxyphenyl) -6-naphthalene was used in place of 1-benz-2- (3-gas-4-amidooxyphenyl) -6- (trans4-propanecyclohexyl) naphthalene, and the same procedure was performed. White crystals of 2- (3-fluoro-4 -cyanophenyl 6-propylnaphthalene were obtained. [Example 29] Synthesis of 2- (3,5-difluoro-4-cyanophenyl) -6-propylnaphthalene In Example 11, except for using 1-fluoro-2- (3,5-difluorophenyl) -6-propylnaphthalene obtained in Example 4 instead of 1-fluoro-2- (3, Except for 5-difluorophenyl) -6- (trans4-propancyclohexyl) naphthalene, the same was performed to obtain 2- (3,5-difluoro-4-cyanophenyl) -6-propylnaphthalene. Crystals. The following compounds were obtained in the same manner as in Examples 2, 7, 8, and 9. 1-fluoro-2- (4-cyanophenyl) -6-ethylnaphthalene 1-IL-2- (4- Cyanophenyl) -6-propylnaphthalene 1-fluoro-2- (4-cyanophenyl) -6-butylene

Page 199 528794 V. Description of the invention (197) 1-Ail-2- (4-cyanophenyl) -6-pentaphthalene 1-gas-2- (4-cyanophenyl) -6-hexylnaphthalene 1-fluoro 2- (4-cyanophenyl) -6-heptaphthalene 1-fluoro ^ 2- (3-gas-4-cyanophenyl) -6-ethylnaphthalene 1-fluoro-2- (3-fluoro-4- Cyanophenyl) -6-Butylnaphthalene1-Dun-2- (3-Ail-4-cyanophenyl) -6-pentaphthalene 1-fluoro-2- (3-fluoro-4-cyanophenyl) -6 -Hexaphthalene 1-fluoro-2- (3-fluoro-4-cyanophenyl) -6-heptaphthalene

1-fluoro-2- (3,5-difluoro-4-cyanophenyl) -6-ethylnaphthalene 1-fluoro-2- (3,5-digas-4-cyanophenyl) -6-butylene 1-Gas-2- (3,5-difluoro-4-cyanophenyl) -6-pentaphthalene 1-fluoro-2- (3,5-difluoro-4-cyanophenyl) -6-hexanaphthalene 1-fluoro-2- (3,5-difluoro-4-cyanophenyl) _6-heptaphthalene

2- (4-cyanophenyl) -6-ethylnaphthalene 2- (4-cyanophenyl) -6-propylnaphthalene 2- (4-cyanophenyl) -6-butylnaphthalene 2- (4-cyanophenyl ) -6-pentaphthalene 2- (4-cyanophenyl) -6-hexylnaphthalene 2- (4-cyanophenyl) -6-heptaphthalene 2- (3-fluoro-4-cyanophenyl) -6- Ethylnaphthalene 2- (3-fluoro-4-cyanophenyl) -6-butyphthalene 2- (3-fluoro-4-cyanophenyl) -6-pentaphthalene 2- (3-xiang-4_cyanophenyl ) -6-hexylnaphthalene 2- (3-fluoro-4-cyanophenyl) -6-heptaphthalene

Page 200 528794 V. Description of the invention (198) 2- (3,5-difluoro-4-cyanophenyl) -6-ethylnaphthalene 2- (3,5-difluoro-4 -cyanophenyl) -6 -Butylnaphthalene 2- (3,5-difluoro-4-cyanophenyl) -6-pentaphthalene 2- (3,5-difluoro-4-cyanophenyl) -6-hexylnaphthalene 2- (3, 5-difluoro-4-cyanophenyl) -6-heptaphthalene 1-gas-2- (4- (4-cyanophenyl) phenyl) -6-ethylnaphthalene 1-mer-2- (4- ( 4-cyanophenyl) phenyl) -6-propylnaphthalene 1-fluoro-2- (4- (4-cyanophenyl) phenyl) -6-butylnaphthalene 1-fluoro-2- (4- (4- Cyanophenyl) phenyl) -6-pentaphthalene

1-fluoro-2- (4- (4-cyanophenyl) phenyl) -6-hexylnaphthalene1-fluoro-2- (4- (4-cyanophenyl) phenyl) -6-heptaphthalene 1- Fluoro-2- (4- (4-cyanophenyl) phenyl) -6- (3-butenyl) naphthalene 1-dun-2- (3-fluoro-4- (4-cyanophenyl) phenyl ) -6-Ethylnaphthalene 1-fluoro-2- (3-fluoro-4- (4-cyanophenyl) benzyl) -6-propylnaphthalene 1-fluoro-2- (3-fluoro-4- (4- Cyanophenyl) phenyl) -6-butylene 1-fluoro-2- (3-fluoro-4- (4-cyanophenyl) phenyl) -6-pentaphthalene 1-gas-4- (4-cyano Phenyl) phenyl) -6-hexylnaphthalene 1-fluoro-2- (3-fluoro-4- (4-cyanophenyl) phenyl) -6-heptaphthalene

1- IL-2- (3-fluoro-4- (4-cyanophenyl) phenyl) -6- (3-butanyl) naphthalene 1-fluoro-2- (3,5-di 4- (4 -Cyanophenyl) phenyl) -6-ethylnaphthalene1-fluoro-2- (3,5 -digas-4- (4-cyanophenyl) phenyl) -6-propylnaphthalene 1-It-2- (3,5 -Digas-4- (4-cyanophenyl) phenyl) -6 -butylnaphthalene 1-fluoro-2- (3,5-difluoro-4- (4-cyanophenyl) phenyl ) -6-pentaphthalene 1-benz-2- (3,5-difluoro-4_ (4-cyanophenyl) phenyl) -6-hexylnaphthalene

Page 201 528794 V. Description of the invention (199) 1-Fluoro-2- (3,5-difluoro-4- (4-cyanophenyl) phenyl) -6-heptaphthalene 1-jiu-2- (3 , 5-Difluoro-4- (4-cyanophenyl) phenyl) -6- (3-butyridinyl) naphthalene 1-fluoro-2-(4-(3-fluoro-4-1-fluoro-2 -(4- (3-fluoro-4-1-fluoro-2- (4- (3-gas-4-1-fluoro-2-(4-(3-fluoro-4-1-fluoro-2-( 4-(3-Ga-4-1-fluoro-2-(4-fluoro-3-1-fluoro-2- (4- (3-fluoro-4-bufluoro-2-(3-fluoro -4- (3-Bufluoro-2-(3-fluoro-4- (3-1-fluoro-2- (3-fluoro-4- (3-1-It-2-(3-gas-4- (3-1-fluoro-2- (3-fluoro-ΙΟ-ΐ- IL-2-(3 -fluoro-4-(3-1-fluoro-2- (3-fluoro-4- (3-cyanobenzene Phenyl) phenyl) -6-bennaphthyl cyanophenyl) phenyl) -6-propylnaphthyl cyanophenyl) phenyl) -6-butylnaphthyl phenyl) phenyl) -6-pentaphthalene cyanophenyl) Phenyl) -6-hexylnaphthalene cyanophenyl) phenyl) -6-heptaphthalene

Cyanophenyl) phenyl) -6_ (3-butenyl) naphthalene-4 -cyanophenyl) phenyl) -6_ethinamer-4-cyanophenyl) phenyl) -6-propylnaphthalene fluoride -4-cyanophenyl) phenyl) -6-butylnaphthylfluoro-4-cyanophenyl) phenyl) -6-pentaphthalenefluoro-4-aerophenyl) phenyl) -6-hexylnaphthalene-4 -Cyanophenyl) phenyl) -6-heptaphthylfluoro-4-cyanophenyl) phenyl) -6- (3-butenyl) naphthalene

1-fluoro-2- (3,5-difluoro-4- (3-fluoro-4-cyanophenyl) phenyl) -6-ethylnaphthalene 1-fluoro-2- (3,5-digas-4 -(3-fluoro-4-cyanophenyl) phenyl) -6-propylnaphthalene 1-fluoro-2- (3,5-difluoro-4 (3-fluoro-4-cyanophenyl) phenyl) -6-Butylnaphthalene 1-fluoro-2- (3,5-diIL-4- (3-IL-4-cyanophenyl) phenyl) -6_pentaphthalene 1-dun-2- (3,5- Difluoro-4- (3-fluoro-4-cyanophenyl) phenyl) -6-hexylnaphthalene 1-gas-2- (3,5-difluoro-4- (3-fluoro-4-cyanophenyl) ) Phenyl) -6-heptaphthalene

Page 202 528794 V. Description of the invention (200) 1-Ail-2- (3,5-difluoro-4- (3-gas-4-cyanophenyl) phenyl) -6- (3-butenyl ) Naphthalene 1-fluoro-2- (4- (3,5-difluoro-4-cyanophenyl) phenyl 6-ethylnaphthalene 1-fluoro-2- (4- (3, 5 -difluoro-4- Cyanophenyl) phenyl) -6-propylnaphthalene 1-fluoro-2- (4- (3, 5-di1-4-cyanophenyl) phenyl) -6-butylnaphthalene 1-fluoro-2- ( 4- (3,5-difluoro-4-cyanophenyl) phenyl) -6-pentaphthalene 1-gas-2- (4- (3,5-digas-4-cyanophenyl) phenyl) -6-Hexaphthalene 1-fluoro-2- (4- (3,5-digas-4-cyanophenyl) phenyl) -6-heptaphthalene 1-fluoro-2- (4- (3,5- Digas-4-cyanophenyl) phenyl) -6- (3-butane) naphthalene 1-fluoro-2- (3-fluoro-4- (3,5-diIL-4-cyanophenyl) Phenyl) -6-ethylnaphthalene 1-fluoro-2- (3- 1-fluoro-2- (3-1-fluoro-2-(3-1-fluoro ^ 2- (3-fluoro-4- (3 , 5 -difluoro-4-cyanophenyl) phenyl) -6-propylnaphthalenefluoro-4- (3,5-diIL-4-cyanophenyl) phenyl) -6-butylnaphthalene IL-4- (3,5 -bis--4-cyanophenyl) phenyl) -6-pentaphthalene-4- (3,5-di-IL-4-cyanophenyl) phenyl) -6-hexanaphthalene 1- Fluoro-2- (3-fluoro-4- (3,5-diIL-4-cyanophenyl) phenyl) -6-heptaphthalene 1-fluoro-2- (3-fluoro-4- (3,5 -Digas-4-cyanophenyl) phenyl)- 6- (3-butenyl) naphthalene 1-dun-2- (3,5-difluoro-4- (3,5-difluoro 4-cyanophenyl) phenyl) -6-ethylnaphthalene 1-fluoro- 2- (3,5-difluoro-4- (3,5-difluoro-4-cyanophenyl) phenyl) -6-propylnaphthalene 1-gas-2- (3,5-difluoro-4- (3,5 -Digas-4-cyanophenyl) phenyl) -6-butylene

Page 203 UC / ργ 22 '... Factory-Note) I ^ J | J 88106446 Modified month f f 12. L6W ^ (»Supplementary Patent Exemption Patent Specification 528794 Chinese Naphthalene Derivatives and Liquid Crystal Compositions Containing Benzene Derivatives Inventor of the name two, Mingfa person three, please apply for the English name (Chinese) First name A surname Yi Guoying living in

G surname G. Hidetake Takehara Hara Osawa Takazu Haruyoshi Negishi Shinji 7 9 8 isl, Inland Saki 7 1¾¾ / 2 (One word Θ 7 Dadai 22g Frmachi 3C71-Limit one 427 Nawaragawa Yui Nakamoto Spring guide t multi-strand j this municipal and district industry | Nikura foot Datiangong Zuo North East Elephant Yibu County Dudu Hua Ye Ye Jing Jing Mo Yi Qian Qian Dong Dong You Guoli] i ^ li Books | Books |曰 曰 曰 曰 λ Social-type plant industry engineering cattle yashita bridge plate β, Zhejing 0 ^ National I textbooks Sanhuang Village No. 8 Fan

6 64 ο 8 8

Page 1 Correction page

528794 Case No. 88106446

lL Month Revision 91 5. ϊ j Revision Page 4 5. Description of the Invention (53) shows a sufficiently high value. Next, (Μ-1) was filled in a TN groove with a thickness of 4.5 // m to prepare a liquid crystal element and its electro-optical characteristics were measured. The result obtained was as follows: 9 8. 6 ° C 4. 60 1. 76V 24. 2m second nematic phase upper limit temperature (Th; dielectric anisotropy (△ ε) threshold voltage (Vth) response time (r) On the other hand, the physical properties of the main liquid crystal (H) alone and electro-optic The characteristics are as follows: the upper limit temperature of the nematic phase (Ty: dielectric anisotropy (△ ε), threshold voltage (Vth), response time (τ)

11 6. 7 ° C 4. 80 1. 88V 21 · 5m seconds Here, the response time is the response time when the rise time (τ r) and the fall time (τ d) become equal. From the above results, it is known that the dielectric anisotropy of (I b-1) is less than (Η), and the threshold voltage is reduced by about 10%. Second, (Ib_2) c3h7 shown in Table I

The compound (ib-2) was added to (ii) at the same ratio (20%) as described above to prepare a liquid crystal composition (M-2). The measurement results of (M) of (M-2) and the electro-optical characteristics measured after the same preparation of the liquid crystal element were as follows:

Nematic phase maximum temperature () 9 2 · 7 ° C

88106446.ptc Page 56 528794_ Wei V. Description of the invention (54) 91.5. 14 88106446_ Year Month Revision 5. 14 Revision page Dielectric anisotropy (ζ \ ε) 5. 7

Threshold voltage (Vth) 1. 53V response time (τ) 28. 0m seconds Therefore it is known that the dielectric anisotropy of '(I b-1) is greater than (η), and the threshold voltage is reduced by about 20%. Furthermore, the results of the thermal stability test and the ultraviolet irradiation test performed in the same manner as in the above-mentioned (M -1) -sample application (M-2) did not show a change in τν ι. In addition, as a result of measuring the voltage holding ratio, it showed a sufficiently high value at the time of preparation, after heating, and after ultraviolet irradiation.

As mentioned above, the compound of the general formula (丨) is very useful for preparing a ① having a wide nematic phase temperature range, ② showing a low threshold voltage, it may be real, low voltage driving, ③ it is possible to achieve high-speed response, and ④ and voltage It is also sufficiently possible to realize a liquid crystal composition driven by an active matrix. (Ic-7) to be shown in Table 2

F

'(k &gt; 7)

In other words, the compound is added with a main liquid crystal composition (H) at a ratio of 20% by weight, and has a wide range of transparency 'having low viscosity, and may also be used in a movable beer driver' to prepare a liquid crystal composition—3 ). Here, the values of the electro-optical characteristics of the liquid crystal element manufactured by (H) and the liquid crystal element manufactured by (Η) are as follows. ··

Nematic phase upper limit temperature (TV) 116. 7 ° C

Tc-N +1 1 ° C

Critical value voltage (V th) 2.14V Dielectric anisotropy (△ ε) 4.8

88106446.ptc Page 57 528794

、 Explanation of the invention (55) Refractive index anisotropy (△ n) 0.090 VL · b, here the correction page, the threshold voltage (Vth) is measured in a TN tank with a thickness of 6 // m and measured at 20 ° C Value. The electro-optical characteristics of the liquid crystal element made with (M-3) and the physical property value of '(M-3) on the other hand are as follows: Τν-1 ΤΝ threshold voltage (Vth) dielectric constant difference Squareness (△ £ Refractive index anisotropy (△ n 120 ° C-2 〇C 2. 06V 5 · 5 .—, 0.110) Because of the addition (I c — 7, but ,,, u should be above 1 ° C . Further) 7 To increase the nematic phase upper limit temperature (τ ^) by 3 u or more, cool this (M-3) to -6 (). C 乂 Measure daily, ^ ,, and, compared with person (Η), the reduction value is as much as 13. It is also known that on the evening of the stable temperature range of nematic phase ^, due to the addition (Ic_7), Increase: = = 16c as much as voltage. In addition, the refraction it # electric rate anisotropy reduces the critical value 1 when the anisotropy of the transmittance Λ is suppressed 0.02. Add to the main liquid crystal ( Η) as a benchmark. Secondly, determine the voltage retention rate of this component's voltage of 80 ° C, which is known as JL Electron, and the welding retention rate is very good. (R-1) for matrix drive

F, —, / ^ \ ύ ^

The naphthyl group was replaced by 1, and the molybdenum was replaced by 2, 6-, 4 1 in the 仁 ′ kernel (Ic ~ 7), and replaced by a benben + (R-1)

Compound with similarity to (Ic-7) F

"The above mentioned phase ratio 1 ^^

88106446.ptc Page 58 528794

Zi14 said Wei 8810fi trend ^ film five, description of the invention (56) '^ ---- · sfe. Add (Η), and prepare a liquid crystal composition (Hr — phase upper limit temperature d) is 1011, # (Μ_ 此 | Cheng: There are many nematics. In addition, its dazzling point u5t :, high second car: 3 '; Guo Er lowered compared to phase (M-3), the warmth of nematic phase thus, and such as Bu Yu, Qi The reduction value of the / degree range is more than 25 t. As mentioned above, in obtaining a wide range of upper and lower thunderbore, the / uI 'degree range loss, low critical value, and the proper refractive index of the liquid crystal have The effect is better than that of the conventional compounds. The general formula (M-3) of the product has (id-1) shown in Table 3.

It is called -ΓΚ wF -F (W-1) compound is added at a ratio of 20% by weight; a kind of liquid crystal composition (H) having a wide temperature range = to prepare a liquid crystal composition (m_4). The physical property value of (^ -1), and the hydraulic property value made with (U-D) are as follows:

Tn-1 critical voltage (vth) dielectric anisotropy (△ ε) response time (I * r = τ d) refractive index anisotropy (△ η) 9 1. 0 ° c 1. 94V 4. 85 2 8 · 4 m seconds 0.112 Therefore, it is learned that due to the addition of (I d-1) 20%, although the nematic maximum temperature (TN-1) is lowered slightly, the response time is not deteriorated and the criticality is reduced. The voltage greatly increases the refractive index anisotropy (about 0 · 0 2 when the main liquid crystal (H) is used as a reference). Next, this composition was left at room temperature for i months, and as a result, no crystal deposition or phase separation was observed. Therefore, we know that (I d — 1)

88106446.ptc Page 59 9! .528794 Case No. 88106446 V. Description of the invention (57) It is known that liquid crystal has excellent compatibility. ° C in order to crystallize and measure its dazzle, this (Id-1) was cooled to _15 On the other hand, the result of (R-2) I was 14 ° C. For F _ F (R-2),: t ^ has a similar structure to (⑷1), but belongs to the biphenyl skeleton. ⑻ is added at the same ratio (20 wt%) as above to prepare 液晶 to prepare a liquid crystal group. HR-2). The same measured physical properties and electro-optical characteristics are as follows:? 8 6. 0 ° C 1. 86V 4. 92 27 · 0m s 0.096 response time becomes faster, the critical value, its nematic phase upper limit temperature (TNM) changes Amend

Correction tribute

^ Nl critical voltage (Vth) dielectric anisotropy (△ ε) response time (rr = τ d) refractive index anisotropy (△ η) "So we know that the voltage compared to (M-1) is also It's only slightly reduced. However, the lower the anisotropy, and the refractive index anisotropy (△ η) also slightly increased

Next ’will be shown in Section 1; (Id —2) F C3H7

F (W-2)

The compound was added to the main liquid crystal (i) at the same ratio (20%) F to prepare a liquid crystal composition (M-5). The physical properties of this composition and the electro-optical characteristics of liquid crystal elements made with this composition are as follows: Tnm 8 5. 1 ° C

528794 Case No. 88106446 Rev. I &gt; · i 4 «Revised page V. Description of the invention (58) Threshold voltage (Vth) Dielectric anisotropy (△ ε) Response time (rr = τ d) Refractive index anomaly (△ η) Therefore, it is known that the phase with (M _ 4) is lower and the refractive index anisotropy is slightly reduced to further reduce the threshold voltage. (Id-7) shown in Table 3 1. 74V5. 7 3 1 · 1 m second 0.107 Although the upper limit temperature of the nematic phase is slightly lowered ′, it has the same high-speed response and c3h7

The compounds of F (W-7) show a nematic phase in the range of melting point-16 ° C to 1 ° C. In contrast, the compound (I d-1) having a similar skeleton structure but having no fluorine substituted in the naphthalene ring is a crystalline substance having a melting point of 6 2 · 5 ° C and does not exhibit liquid crystallinity. The general nematic liquid crystal is added and the upper limit of the nematic phase obtained by the extrapolation method (TNM) is -12 c, so the liquid crystal (Id-7) is more excellent. It was found that although the melting point was lowered by the introduction of fluorine into the naphthalene ring in the compound of the general formula (I d-7), the liquid crystallinity was not lowered. The compound of the above (Id-7) was added to the main liquid crystal composition (H) at a ratio of 20% by weight to prepare a liquid crystal composition (M-6).

Tn-i threshold voltage (V t h) dielectric anisotropy (△ £ refractive index anisotropy (△ n)

8 6. 0 ° C 12 t: 1. 65V 6. 5 0.107 Page 61 528794 ^ 14 ft i

31.528794 Case No. 88106446 Amendment May · I 4 Rev. 'Main page V. Description of the invention (70) 1-Gas-2- (3-IL-4-chlorophenyl) -6-pentaphthalene 1-fluoro-2- (3-Fluoro-4-Gaphenyl) -6-hexylnaphthalene 1-fluoro-2- (3-Ga-4-chlorophenyl) -6-heptaphthalene 1-IL-2- (3-chlorophenyl ) -6- (3-butenyl) naphthalene 1-H-2- (3,5-digas-4-gasphenyl) -6_ ethylnaphthalene 1-H-2- (3,5-difluoro- 4-Gasphenyl) -6-propylnaphthalene 1-IL-2- (3,5-difluoro-4-gasphenyl) -6-butylnaphthalene 1-fluoro-2- (3,5-difluoro-4 -Phenylphenyl) -6-pentaphthalene 1-fluoro-2-(3,5-difluoro ^ 4-phenylphenyl) -6-hexylnaphthalene

1-Lan-2- (3,5-difluoro-4-Gaphenyl) -6-heptaphthalene 1-IL-2- (3,5-difluoro-4-chlorophenyl) -6- (3 -Butenyl) naphthalene 1-H-2- (4-trifluoromethoxyphenyl) -6-ethylnaphthalene 1-gas-2- (4-trifluoromethyloxyphenyl) -6-propylnaphthalene 1- Fluoro * -2- (4-triILfluorenyloxyphenyl) -6-butylene 1-benzyl-2- (4-trifluorofluorenyloxyphenyl) -6-pentaphthalene 1-H-2- (4- Trifluorofluorenylphenyl) -6-hexylnaphthalene 1-fluoro-2- (4-trifluoromethoxyphenyl) -6-heptaphthalene 1_IL-2- (4-trifluorofluorenyloxyphenyl) -6 -(3-Butyl) naphthalene

1-H-2-(3-IL-4-trifluorofluorenyloxyphenyl) -6-ethylnaphthalene 1-gas-2-(3-gas-4-trifluorofluorenyloxyphenyl) -6-propylnaphthalene 1-Gas-2- (3-Lan-4-trifluorofluorenyloxyphenyl) -6-butylnaphthalene 1-fluoro-2- (3-fluoro-4-trifluorofluorenyloxyphenyl) -6-pentaphthalene 1-fluoro-2-(3-fluoro-4-trifluorofluorenyloxyphenyl) -6-hexylnaphthalene 1-IL-2-(3-fluoro-4-trifluorofluorenyloxyphenyl) -6-heptaphthalene

88106446.ptc p. 73 528794

1-fluoro-2-(3,5-difluoro-4 -difluorofluorenyloxy) -6-pentaphthalene 1-fluoro-2- (3,5-difluoro-4-difluoromethoxyphenyl) ) -6-hexylnaphthalene 1-fluoro-2- (3, 5-difluoro-4-difluoromethoxyphenyl) -6-heptaphthalene 1-fluoro ^ 2- (3,5-difluoro-4_ Di-IL methoxyphenyl) -6- (3-butanyl) naphthalene 1-II-2- (4-trifluoroi-tolyl) -6-ethylnaphthalene 1-town-2- (4-trifluorotolyl) ) -6-propylnaphthalene 1-fluoro-2- (4-tri-tolyl) -6-butylnaphthalene 1-IL-2-(4-trifluoroi-tolyl) -6-pentaphthalene

1-fluoro-2- (4-trifluorofluorenyl) -6-hexylnaphthalene 1-fluoro-2- (4-trifluorotolyl) -6-heptaphthalene 1-fluoro-2-(4-trifluoro Tolyl) -6- (3-butenyl) naphthalene 1-gas-2- (3-fluoro-4-trifluorofluorenylphenyl) -6-ethylnaphthalene 1-fluoro ^ -2- (3-fluoro- 4-trifluorofluorenylphenyl 6-propylnaphthalene 1-fluoro-2- (3-fluoro-4-trifluorotolyl) -6-butylnaphthalene 1-IL-2- (3-fluoro-4 -tri-It 曱Phenyl) -6-pentaphthalene 1-fluoro-2- (3-fluoro-4-trifluorofluorenylphenyl) -6-hexylnaphthalene 1-fluoro-2- (3-fluoro-4-tris-fluorenylphenyl) ) -6-heptaphthalene 1-IL-2-(3- | 1-4 -trifluorotolyl) -6- (3 -butylfluorenyl) naphthalene 1-fluoro-2-(3,5-difluoro- 4-trifluorotolyl)-6-ethylnaphthalene 1-fluoro-2-(3,5-difluoro-4 -trifluorofluorenylphenyl) -6-propylnaphthalene 1-gas-2- (3,5- Digas-4 -trifluorofluorenylphenyl) -6-butylnaphthalene 1-gas-2- (3,5-difluoro-4-trifluorofluorenylphenyl) -6-pentaphthalene1-benzyl-2-( 3,5-difluoro-4_trifluorofluorenylphenyl) -6-hexane

88106446.ptc page 75 2000.01.10.075 correction page 528794

Alkyl ~ 4 ~ yl) naphthylene dicyclohexyl Case No. 88106446 V. Synthesis of the invention (172) [Example 1 7] In Example 14, 5, 6 was used and dicyclohexane-4, 4 '- The diketomonoacetic acid was replaced by ^ 5,6 -digas-2- (trans 4'fluoro-bromonaphthalene in place of 6-naphthylacetal in place of naphthone, and the reaction was also performed, followed by Removal of hexamethyl 4,6- (5,6-difluoronaphthyl) bicyclohexane-4-i with formic acid was carried out. The same was obtained on ice, and methoxymethyltriphenyl chloride was obtained. The scale and the third potassium butoxide are made of: wei = zhong, and the above-mentioned solution of trans 4,-(5,6, phenylphenyl) -4-one in THF is added dropwise at 0 mT. After reacting for 1 hour The organic layer was concentrated. The hexane was added to dissolve the organic layer. Hexane was added to dissolve it, and the solution was concentrated. After adding triphenylphosphine oxide, it was concentrated with a mixed solvent of methanol / ㈣Λ The organic layer was used to dissolve the obtained crude product in acetone / wood ^ t „af 〇V,:; Diluted hydrochloric acid was neutralized, and it was taken out by using benzyl. The organic layer was used: water was used for cleaning, and it was dehydrated with anhydrous sodium sulfate Drying. Distilling off the solvent to obtain trans-4, ^ = fluoronaphthalene 1 dicyclohexyl'a-4, a carbon aldehyde crystal. It is used with a weiji reagent made from ^ jietian lactamyl diphenyl pin and the third potassium butoxide; Fluorine K trans 4, _ ethylene dicyclohexyl benzene can also be obtained from the following compounds; Nai 5 '6-difluoro-2- [trans 4' ~ (3_ butenyl) bicyclohexane + yl] naphthalene 6-fluoro-2- (trans 4'-ethylenedicyclohexane_4_yl) naphthalene "6-fluoro-2-([4 '-(3-butenyl) biscyclohexane + yl] naphthalene 5, 6 '7-Digas-2- (trans 4', ethylene dicyclohexyl _ [yl] naphthalene 5 '6, 7-trifluoro-2- [trans 4'-(3-butanyl) dicyclohexyl _ 4-yl] naphthalene

88106446.pt Page 175 528794 Λ_η Case No. 88106446 Fifth, the description of the invention (173) ---- ^ 4,5, 6, 7 -tetrafluoro-2- (trans 4'-ethylenedicyclohexane-4 -yl ) Naphthalene 4,5,6,7-tetrafluoro-2- [trans 4 '-(3 -butenyl) bicyclohexane-4 -yl] naphthalene 6-gas-2- (trans 4-ethenylcyclohexyl ) Naphthalene 6-fluoro-2- [trans 4- (3 -butenyl) cyclohexyl] naphthalene 5,6-difluoro-2- (trans 4-ethenylcyclohexyl) Cai 5,6-difluoro-2 -[Trans 4- (3-butenyl) cyclohexyl] naphthalene 5,6,7-trifluoro-2- (trans 4-ethenylcyclohexyl) naphthalene 5,6,7 -trifluoro-2- [trans Synthesis of 4- (3-butanyl) cyclohexyl] naphthalene [Example 18] 5, 6-difluoro-2- [4- (trans 4-propcyclohexyl) phenyl] naphthalene For a compound consisting of 5, 6 -THF solution of a lithium metal reagent made of difluoro-2-bromonaphthalene, and under ice cooling, 4-iodo-1- (4-transpropyl) cyclohexylbenzene and a catalyst amount of triphenylphosphine palladium are added dropwise. (0) in THF, and then stirred at room temperature for 3 hours. Water and toluene were added to stop the reaction, and dilute hydrochloric acid was added until the water layer became weakly acidic. It was extracted with toluene, and the organic layers were combined, washed sequentially with water, saturated brine, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The obtained oil was purified by silica gel chromatography (hexane), and then recrystallized from ethanol to obtain 5, 6-difluoro-2- [4- (trans 4- Propylcyclohexyl) phenyl] naphthalene white crystals. The following compounds can also be obtained. 5,6-difluoro-2- [4- (trans4-ethylcyclohexyl) phenyl] Cai 5,6-difluoro-2- [4- (trans 4-butcyclohexyl) phenyl] naphthalene 5, 6-Digas-2- [4- (trans 4-pentylcyclohexyl) phenyl] naphthalene

88106446.ptc page 176 amended buy 528794 Λ _____ 3. Case No. 88106446 said 5. Description of the invention (181) L. methanol / water = 1/1 mixed solvent washes. The organic layer was concentrated, and the obtained crude product was dissolved in ethanol. To this was added an ethanol solution of hydrogen hydroxide, and the mixture was stirred at room temperature for 1 hour. Water was added to the solution, and the solution was neutralized with dilute hydrochloric acid, followed by extraction with toluene. The organic layer was washed with water, and then dried over anhydrous sodium sulfate. The solvent was distilled off to obtain crystals of trans 4 '-(1-fluoro-2 -trifluoroamidino-6-yl) bicyclohexane-trans 4-carboxaldehyde. It was reacted in the same way as a carbamidine reagent made from phosphonium iodide triphenyl scale and potassium tert-butoxide, and thus 1-fluoro-2 -trifluorofluorenoxy-6- (trans 4 ' -Ethylenebicyclohexane-trans 4-yl) naphthalene. The following compounds can also be obtained. 2-trifluoromethoxy-6- (trans 4'-ethylenebicyclohexane-4-trans-yl) naphthalene 2-trifluoromethoxy-6-[trans 4 '-(3 -butenyl) bicyclo Hexane-6-trans 4-yl] naphthalene 1-fluoro-2-trifluorofluorenyloxy-6- [trans 4 '-(3-butanyl) bicyclohexane-trans 4-yl] naphthalene 1,3 _Difluoro 2 -trifluorofluorenyloxy-6- (trans 4'-ethylene dicyclohexyl-4 -trans-yl) naphthalene 1,3-difluoro-2 -trifluorofluorenyloxy-6-[( Trans 4 '-(3-butane'yl) bicyclohexane-4-trans-yl] naphthalene 1,3,8-trigas-2 -trifluoro 1-methoxy-6- (trans 4' -ethene Bicyclohexyl-4-trans-yl) naphthalene 1,3,8-trigas-2-trifluoromethoxy-6-[[trans 4 '-(3-butane) bicyclohexane-4-trans -Yl] naphthalene 2 -trifluoromethoxy-6_ (trans 4-ethenylcyclohexyl) naphthalene

88106446.ptc page 184 correction page 528794 4; _3

Case No. 88106446 V. Description of the invention (182) 2-trifluoromethoxy-6-[trans 4-(3-butenylfluorene ^ 1 -fluoro-2-difluoromethoxy-6-(trans 4- Ethyl Yan I said that -2-trifluoromethoxy. [Trans 4 — (3-diyl), 1,3-difluoro-2-trifluorofluorenyl-6 — (trans 4-ethyl 5 Hexyl] naphthalene 1,3-difluoro-2-trifluorofluorenyloxy-6- [trans- 4-((3,% hexyl) naphthalene] naphthalene [Example 23] 1-fluoro-2-trifluoromethoxy-6- (4 ~ fine group) cyclohexyl] naphthalene makes 34g of 4-propenylboronic acid (this compound is a kind of basic group) naphthalene synthesis of Grenia reagent and lysopenic acid trimethylglycerin. Stupid benzene, 46ml of ethanol, and 92ml of water, g / ml of 92ml of osmium and sulfamidine rmi 1 To this was added 25.5g of potassium carbonate and osmium palladium (〇) 1.3111§, and at 75 ° C g add water and toluene, then add dilute hydrochloric acid, n. stop. extract by toluene, combine organic reeds, wash the weak acidity of the water layer, and dry it by anhydrous sodium sulfate; two members ^, and Η4-Propylphenyl) naphthalene_2_pan 41.4§ was obtained. 12.7 g of this 6- (4-propenylphenyl) ^-2-phenol was dissolved in 50 ml of dichloromethane. Add N-fluoro-tris-trimethoxine-2-sulfonate 13.1 lg and stir at room temperature for 18 hours. After that, perform the same treatment as above, and the obtained oily substance is subjected to silica gel chromatography. (Hexane / ethyl acetate = 9/1), and 10-fluoro-6- (4-propylphenyl) naphthalene-2-phenol 10 g was obtained. Hereinafter, it was changed to the same as in Example i. Difluorofluorene was oxidized for sulfonium dithiocarbonate to obtain 2.3 g of the title 1-fluoro-2-trifluoromethoxy-6- (4-propylphenyl) naphthalene. [Example 24] Of 1,3-Difluoro-2-trifluorofluorenyloxy-6- (4-propanephenyl) naphthalene

88106446.ptc Page 185 528794 V. Description of the invention (183) Case number 88106446 Synthesis of 89. Supplement: Make 7.3 g of 4-propenylboronic acid and difluoromethanesulfonic acid l 3_difluoro__2_trinaphthalene-1 6-vinegar i lg (this-compound is based on trifluoromethanesulfonate: methoxynaphthalene-6-hours with triflate oxalate acetic acid to contain a 5_ 'triphenylphosphine 0.4g, and in 85t Add water and toluene to this, extract the water sound by toluene, and mix and mix 8 small #. Water, saturated brine was washed successively, and several layers' purified with ethyl acetate / ethyl acetate /]) Alcohol = ^ gel gel chromatography to 1,3-a hydrazine-2-trifluoromethoxy_6_ (4_probendimidine π, said, and [Example 25] 1- 款 _2_ Three gas f 'gas, crystal 6.3 g. Synthesis of 4 ~ propylphenyl) naphthalene In Example 23, except the use of 2-fluoro-4-phenyl glutamic acid, all were carried out in the same manner, to obtain rigid propyl : Pentamic acid instead of [propyl-6- (2-fluoro-4-propylphenyl) naphthalene. 2 Difluoromethoxy is the same as in Example 23, 24, or 25. The following methods can obtain the following human fluorenyloxy ~ 6- (4-propylphenyl) naphthalene 2_diranoxane lactyl 4- (4-pentylphenyl) extracted TiC (4-heptylphenyl: oxy ~ 6_ (4 ~ pentylbenzyl) extracted 1,3-difluoro-2-trifluoromethoxy-6 ~ yl) benzyl] naphthylbenzyl) naphthalene 88106446.ptc § page 186 amendment 528794_Ά case No. 88106446 V. Description of the invention (184) 1,3-difluoro-2_trifluoromethoxy-6- (4-heptylphenyl) naphthalene 1,3-difluoro-2-trifluorofluorenyloxy-6 -[4-(3-Butanediyl) phenyl] naphthalene 1,3,8-trifluoro-2-trifluoromethoxy-6- (4-fluorenyl) naphthalene 1,3,8-trifluoro -2 -Trilactamyloxy-6- (4-heptylphenyl) naphthalene 1,3,8-triIL-2 -trifluoromethoxy-6- [4- (3-butane) phenyl ] Naphthalene 2-trifluoroi-methoxy-6- (2-dun-4-propylphenyl) naphthalene 2-trifluorobioxo-6- (2-fluoro-4_pentylphenyl) naphthalene 2-tris Fluoro-1 methoxy-6- (2-fluoro-4 -heptyl) naphthalene 2-trifluorofluorenyloxy-6- [2-fluoro-4-(3-butanyl) phenyl] naphthalene 1- Fluoro-2-trifluoromethoxy-6- (2-dun-4 -pentylphenyl) naphthalene 1-fluoro-2 -trifluoromethoxy-6-(2-fluoro-4 -heptylphenyl) naphthalene 1-fluoro-2-trifluoromethoxy-6- [2-benzyl-4- (3-butenyl) phenyl] Naphthalene 2 -trisitoxy-2-trifluorofluorenoxy-2-tridecylmethoxy-2 -trifluorofluorenoxy-1-fluoro-2-trifluoromethyl 1-fluoro-2-triazine Methyl 1-fluoro-2_trifluoromethyl 1-IL-2-trifluoromethyl 1,3-difluoro-2-tri 1,3-digas-2-tri 6- (2,6-difluoro-4 -Propylphenyl) naphthalene 6-(2,6-diden-4 -pentylphenyl) naphthalene 6- (2, 6-difluoro-4-heptylphenyl) naphthalene 6-[2,6-diH- 4- (3-butenyl) phenyl] naphthyloxy-6- (2,6-oxy-6- (2, 6-oxy-6- (2, 6-oxy-6- [2, 6-fluoro-4-propylphenyl) naphthalenefluoro-4-pentylphenyl) naphthalenefluoro-4-heptylphenyl) naphthalene-4- (3 -butylfluorenyl) phenyl] fluorofluorenoxy-6- (2-fluoro-4-propylphenyl) naphthalene IIfluorenyl-6- (2-fluoro-4-pentylphenyl) naphthalene

I

88106446.ptc page 187 amended buy 528794 case number 88106446 supplemented 1,3-difluoro-2 -trifluoro ^ methoxy-6-(2-IL-4 -heptylphenyl) naphthalene 1,3-difluoro ^ 2-trifluoromethoxy-6-[2-fluoro-4- (3-butenyl) phenyl] V. Description of the invention (185) Chua 1,3 -dibenzyl-2 (2,6-difluoro-4-propylphenyl) naphthalene 1,3-di 1,3-di 1,3-diH_2 -trifluoromethoxy-6-(2,6-difluoro-4- Amylphenyl) naphthalenefluoro-2-triILfluorenyloxy-6- (2,6-difluoro-4-heptylphenyl) naphthalene gas-2 -triILfluorenyloxy-6-[2,6-di GA-4- (3-butenyl) phenyl] naphthalenetrifluorofluorenyloxy-6- [4- (trans-4 2-trifluoromethoxy-6- [4- (trans-4 2-trifluoromethyl) Oxy-6- [4- (trans-4 2-trifluoromethoxy-6- [4- (trans-4 1-fluoro-2-trifluorofluorenyloxy-6- [4 1-fluoro-2-tri Fluorofluorenyl-6- [4 1-fluoro-2 -trifluoroimethoxy-6- [4 1-gas-2-trifluoromethoxy-6- [4 1,3-difluoro-2 -Trifluoromethyloxy-1,3-difluoro-2-trifluoromethoxy- -ethylcyclohexyl) benzene-propanecyclohexyl) benzene-butylcyclohexyl) benzene-pentylcyclohexyl) benzene- (trans-4 -B-cyclohexane and 4-propanecyclohexane- (trans 4-butcyclohexane- (trans 4-pentanecyclohexa 6- [4- (trans 4-ethyl 6- [4- (trans 4-propane 1,3 - Fluoro-2-trifluorofluorenoxy-6- [4- (trans 4-butane 1,3-difluoro-2-trifluorofluorenoxy-6- [4- (trans 4-penta-1,3,8 -Trifluoroα-2-trifluoromethoxy-6- [4- (trans 4-yl] naphthyl] naphthyl] naphthyl] naphthyl] naphthyl) phenyl] naphthyl) phenyl] naphthyl) phenyl ] Naphthyl) phenyl] naphthylcyclohexyl) phenyl] naphthylcyclohexyl) phenyl] naphthylcyclohexyl) phenyl] naphthylcyclohexyl) phenyl] naphthylethylhexyl) phenyl] naphthalene 1,3,8- Trifluoro ^ 2-trifluorofluorenyloxy-6- [4- (trans4-propanecyclohexyl) phenyl] naphthalene

88106446.ptc page 188 amended buy 528794 _ case number 88106446_ year month said in / a repair "^ &gt; t_

V. Description of the Invention (189) I Buyi J 1-fluoro-2-trifluorofluorenyloxy-6- [2,6-difluoro-4- [2- (trans 4-pentylcyclohexyl) ethyl] benzene Yl] naphthalene 1,3-difluoro-2 -trifluoromethoxy-6-[2,6-difluoro-4- [2- (trans 4-propcyclohexyl) ethyl] phenyl] naphthalene 1, 3-di | t_2 -trifluoromethoxy-6- [2,6-difluoro-4- [2- (trans 4-pentylcyclohexyl) ethyl] phenyl] naphthalene 4 '-ethyl-4- ( 2-trifluoromethylnaphthalene-6-yl) biphenyl 4'-propyl-4- (2-trifluoromethoxynaphthalene-6-yl) biphenyl 4'-butyl-4-(2-trifluoro Methoxynaphthyl-6-yl) biphenyl 4'-pentyl-4-(2-trifluoromethylnaphthyl-6-yl) biphenyl 4 '-(3 -butanyl)-4-(2-tri Fluoroxonaphthyl-6-yl) biphenyl 4 '-ethyl-4- (1-milk-2 -trifluoromethoxynaphthalene-6 -yl) biphenyl 4' -propyl-4- (1-fluoro -2 -Trifluoromethoxynaphthalene-6-yl) biphenyl 4 '-butyl-4- (1-fluoro-2 -trifluoromethoxynaphthalene-6 -yl) biphenyl 4' -pentyl-4- (1-Lan-2 -trimethoxynaphthalene-6-yl) biphenyl 4 '-(3-butanyl) -4-(1-fluoro-2 -trifluoromethoxynaphthalene-6-yl) bi Benzene 4 '-ethyl-4- (1,3-difluoro-2 -trifluoronaphthalene-6-yl) biphenyl 4' -propyl-4- (1,3-difluoro-2 -tri Fluoromethoxynaphthalene-6-yl) biphenyl 4'-butyl-4-(1,3-difluoro-2-trifluoromethylnaphthalene-6-yl) biphenyl 4'-pentyl-4- ( 1,3 -difluoro-2-trifluorofluornaphthalene-6-yl) biphenyl 4 '-(3 -butanyl) -4- (1,3-difluoro-2 -trifluoromethoxynaphthalene- 6-yl) biphenyl 2'-fluoro-4'-ethyl-4-(2-trifluorofluorenapene-6-yl) biphenyl 2'-fluoro-4'-propyl-4- (2- Tri-IL-methoxynaphthalene-6-yl) biphenyl 2'-fluoro-4'-butyl-4- (2-trifluoromethoxynaphthalene-6-yl) biphenyl

88106446.ptc Page 192 Amendment Page 528794 Case No. 88106446 January ... 'Amendment V. Description of Invention (190) 2, -Fluoro-4 2' -Fluoro-4 2, -Fluoro-4 2 '-Fluoro- 4 2 '-Fluoro-4 2' -Fluoro-4 2 '-Fluoro-4 Benzene 2' -Fluoro-4 2 '-Fluoro-4 2' -Fluoro-4 2, -Fluoro-4 2 '-Ga-4 Base) biphenyl-penta- (3-ethyl-propane-butyl-penta- (3 trace 2: p-pyridine supplementation group 4- (2-trifluoromethoxynaphthalene-6-yl) biphenyl-butanyl) -4-(2-trifluoromethoxynaphthalene-6-yl) biphenyl-1 4-(; [-fluoro-2-trifluoromethoxynaphthalene-6-yl) biphenyl-4-(1-fluoro -2 -Tridenamin-6-yl) biphenyl-4- (1-fluoro-2-trifluoromethoxynaphthalene-6-yl) biphenyl-4- (1-fluoro-2 -tri Fluoromethoxynaphthalene-6-yl) biphenyl-butanyl) -4-(1-lactate-2-tristrimethoxynaphthalene-6-yl) bi-ethyl-4- (1,3--propyl 4- (1,3-fluoromethoxynaphthalene-6-yl) biphenylfluoronaphthyl-6-yl) biphenylfluoromethoxynaphthalene-6-yl) biphenyl H ~ 2-Fluoro-2- Methyl-4- (1,3-difluoro-2-fluoro-2-trifluoromethoxynaphthalene-6-yl) biphenyl-pentyl-4- (1,3-,-(3 -butane) -4- (1,3-difluoro-2-trifluoronaphthalene-6- 3, 5-difluoro-4, 3,5-difluoro -4 '3,5 -difluoro-4' 3,5 -dimorph-4 '3, 5-difluoro-4, 3,5-difluoro-4' 3,5 -ditown-4 '3, 5 -digas-4 '3, 5-difluoro-4, -ethyl-4-(2-tridunyloxycae-6-yl) biphenyl-propyl-4- (2-trifluorofluorenyloxy Naphthalene-6-yl) biphenyl-butyl-4-(2-trifluoromethylnaphthalene-6-yl) biphenyl-pentyl-4- (2-trifluoromethoxynaphthalene-6-yl) biphenyl -(3-Butanediyl) -4- (2-trifluorofluorenoxy-6-yl) biphenyl-ethyl-4- (1-H-2-trioxonaphthyl-6-yl) biphenyl -Propyl-4- (1-fluoro-2-trifluorofluorenaphalyl-yl) biphenyl-butyl-4-0-fluoro-2-trifluorocarbazinyl-6-yl) biphenyl-pentyl -4- (1-Lan-2-triazine-6-yl) biphenyl

I

88106446.ptc Page 193 Amendment page 528794 Case No. 88106446 Λ_η η V. Description of the invention (191) 3,5-difluoro-4 '-(3-butane)-4- (1-Gas-2 -trifluoro i methoxynaphthalene-6-yl) biphenyl 3,5-di-4'-ethyl-4-(1,3 -digas-2 -tritownyl-6-yl) biphenyl 3,5- Difluoro-4'-propyl-4- (1,3-difluoro-2 -trifluorofluorenapene-6-yl) biphenyl 3,5-difluoro-4'-butyl-4- (1 , 3

Ha-2-trifluoromethoxynaphthalene-6-yl) biphenyl 3,5-diquino-4 '-pentyl-4- (1,3 -difluoro-2-trifluoromethoxynaphthalene-6 -yl ) Biphenyl 3,5 -difluoro-4 '--butenyl) -4- (1,3-difluoro-2-trifluoromethoxynaphthalene-6-yl) biphenyl-fluoro-4'- Fluoro-4 '--Fluoro-4, --Gas-4' --Gas-4 '--Fluoro-4' --Just-4 '--Fluoro-4' --Fluoro-4, --Ethyl- 4- (6-trifluorophosphonaphthyl-2-yl) biphenylpropyl-4- (6-trifluorophosphonaphthalene-2 -yl) biphenylbutyl-4- (6-trifluoromethoxynaphthalene -2 -yl) biphenylpentyl-4-(6-trifluorofluorenaphenyl-2 -yl) biphenyl (3-butenyl) -4-(6 -tridecylmethoxynaphthalene-2 -yl) Biphenylethyl-4- (bufluoro-2 -trifluoromethoxynaphthalene-6-yl) biphenylpropyl-4-U-fluoro-2 -trifluoromethoxynaphthalene-6 -yl) biphenylbutyl -4- (1-fluoro-2 -trifluoromethoxynaphthalene-6-yl) biphenylpentyl-4_ (1-fluoro-2-trifluoromethoxynaphthalene-6-yl) biphenyl-fluoro_4 ' -(3-Butanediyl) -4- (1-fluoro-2-triazine-6-yl) biphenyl

88106446.ptc page 194 correction page

Lying 12 "6 Revised Date 骖 iC 528794 -me _ Case No. 88106446 __Year Month 5. Description of the Invention Fluoromethoxynaphthalene-6-yl) biphenyl 3-fluoro-4'-propyl-4- (1,3-difluoro-2-trifluorofluornaphthyl-6-yl) biphenyl 3-fluoro-4 '-Butyl-4- (1,3-difluoro-2 -trifluorofluorenapene-6-yl) bibenzyl 3-fluoro-4' -pentyl-4- (1,3-difluoro_2 -Trifluoromethoxynaphthalene-6-yl) biben 3 -fluoro-4 '-(3-butenyl) -4- (1,3-difluoro-2-trifluoromethoxynaphthalene-6-yl) Biphenyl [Example 26] Synthesis of 1-fluoro-2 -trifluoromethoxy-6- (4-propphenyl) acetylene

10 g of 4-propyl-1-acetylenebenzene and 19.5 g of 2-bromo-5-fluoro-6-trifluoromethonaphthalene were dissolved in 50 ml of N, N-dimethylformamide (DMF). Add 50 mg of copper (I) and 0.1 mg of triphenylphosphine (Q), and stir for $ hours at room temperature. To this was added methylbenzyl, the insoluble matter was filtered off, and then washing was performed with water and saturated saline. After removing the solvent, it was purified by silica gel chromatography (hexane / acetic acid ^ vinegar di 9/1), and then recrystallized by ethanol to obtain fluoro ~ 2 ~ Sanwen = yl-6_ (4-propylbenzyl ) Crystal of acetylene naphthalene 8.6g. * Milk is also available in the following compounds.

2-difluoromethoxy-6- (4-ethylphenyl) ethynylnaphthalene 2-difluoromethoxy-6- (4-propphenyl) ethynylnaphthalene 2- ^ dimonyloxy-6- (4 -Butylphenyl) ethynylnaphthalene 2-digasmethoxy-6- (4-pentylphenyl) ethynylnaphthalene 2-difluoromethoxy-6- [4- (3-butenyl) phenyl] ethynylnaphthalene 1-sin-2- ^ fluorofluoroxy-6- (4-ethylphenyl) ethynylnaphthalene "fluoro-trifluoromethoxy-6- (4-butylphenyl) ethynylnaphthalene Fluorofluorenoxy-6- (4-pentylphenyl) acetylene naphthalene

88106446.ptc page 195 amendment page 528794 case number 88106446 said 89. \ i. .- V. Description of the invention (193) Shizheng supplement 1-fluoro-2-trifluoromethoxy-6- [4- (3- Butenyl) phenyl] acetylene naphthalene 1,3-digas-2-tri 1,3-digas-2-tri 1,3-digas-2 -tri 1,3-digas-2-tri 1 , 3-Digas-2-tri-2-trifluorofluorenoxy-2-triamyloxy-fluoromethoxy-6- (4-ethylphenyl) ethinaphthylfluoro-6- ( 4-propylphenyl) ethynylnaphthylfluoromethoxy-6- (4-butphenyl) ethynylnaphthylfluoromethoxy-6-(4-pentylphenyl) ethynylnaphthylfluorenyloxy-6- [4- (3-butenyl) phenyl] naphthyl 6- (2-fluoro-4_ethylphenyl) acetylene naphthalene 6- (2-fluoropropylphenyl) acetylene naphthalene 2-trifluorofluorenyloxy-6- ( 2 -fluoro-4-butylphenyl) acetylene naphthalene 2 -trifluorofluorenyloxy-2 -trifluoromethoxy-1-fluoro-2-trifluoromethyl 1-gas-2 -trifluorofluorene 1-fluoro- 2-trifluoromethyl 1-gas-2-trifluoromethyl 1-fluoro-2 -trifluoronaphthalene 1,3-di 1,3-di 1,3-di 1,3-di 1,3-diethyl Fast Qin fluoro-2 -fluoro-2 -fluoro-2 -fluoro-2 -fluoro-2-6- (2-dun-4 -pentylphenyl) ethinaphthalene 6-[2-benz-4- (3- Butyl) phenyl] ethynylnaphthyloxy-6- (2-H-4-ethylbenzene ) Acetylene naphthyloxy-6- (2-fluoro-4-propylphenyl) acetylene naphthyloxy-6- (2-fluoro-4-butphenyl) acetylene naphthyloxy-6- (2-fluoro-4 -Pentylphenyl) ethynylnaphthyloxy-6- [2-fluoro-4- (3-butanyl) phenyl] ethoxy-methoxy-6- (2-Ga-4-ethphenyl) acetylene Naphthylfluoromethoxy-6- (2-fluoro-4-propylphenyl) ethynylnaphthalenefluoromethoxy-6- (2-fluoro-4 -butphenyl) ethynylnaphthalenefluoromethoxy-6-(2 -Fluoro-4 -pentylphenyl) ethynylnaphthylfluoromethoxy-6- [2-fluoro-4- (3-butenyl) phenyl]

88106446.ptc Page 196 Correction page

II 528794 Case No. 88106446 said ~~ _ 丄 丨 一 ------------- also 89.12. \ G Η ^ year 卩 · modified ethynyl) ethynylnaphthylphenyl) ethyne Naphthalene 6- (2,6-difluoro-4-butylphenyl) ethoxybenzene 5. Description of the invention (194) 2-trifluorofluorenyloxy-2-trifluorofluorenyloxy-2-trifluorofluorenyloxy -2_trifluorofluorenoxy-2_trifluorofluorenoxy-1-fluoro ^ 2-trifluoromethyl 1-fluoro-2 -trimermethyl 1-town-2_trifluoromethyl 1-fluorene-2- Trifluoromethane 1-fluoro ^ 2_trifluoroamidine 6-(2,6 -difluoro-4 -6- (2,6-difluoro-4- 6-(2,6-difluoro-4-6- [2, 6-difluoro-4-oxy-6- (2, 6-dioxy-6- (2, 6-dioxy-6- (2,6-dioxy-6- (2 , 6-dioxy-6- [2, 6-dipentylphenyl) ethynylnaphthalene (3-butenyl) phenyl] ethynylnaphthylfluoro-4-ethylphenyl) ethinaphthylfluoride 4-propenebenzene Ethoxy) naphthylfluoro-4-butylphenyl) acetylene naphthylfluoro-4 -pentylphenyl) acetylene naphthyl-4- (3-butenyl) phenyl] acetylene naphthalene 1,3-difluoro-2 -tri Fluorofluorenyl-6- (2,6-difluoro-4-ethylphenyl) ethynylnaphthalene 1,3-difluoro-2 -trifluorofluorenyl-6- (2,6-difluoro-4- Propylphenyl) naphthyl 1,3-digas-2-trifluorofluorenyloxy-6- (2,6_di -4-Butylphenyl) ethinaphthalene 1,3-difluoro-2-trifluorofluorenyloxy-6- (2,6-digas-4 -pentylphenyl) acetylene naphthalene 1., 3-difluoro -2 -trifluorofluorenyloxy-6- [2,6-difluoro-4- (3-butenyl) phenyl] ethoxyquin 6- [4- (trans4-propanecyclohexyl) phenyl] Acetylene naphthalene 6- [4- (trans 4-butanecyclohexyl) phenyl] acetylene naphthalene 2-trifluorofluorenyloxy-2-trifluorofluorenyloxy-

88106446.ptc Page 197 Correction page I528794 Case No. 88106446 9L 5. Correction t &gt;. 14 Correction page V. Description of the invention (201) 1-Fluoro-2- (3, 5-difluoro-4_ (3 , 5-difluoro-4-cyanophenyl) phenyl) -6-pentaphthalene 1-fluoro-2- (3,5-difluoro-4- (3,5-difluoro-4-cyanophenyl) Phenyl) -6-hexylnaphthalene 1-fluoro-2- (3, 5-difluoro-4- (3, 5-difluoro-4 -cyanophenyl) phenyl) -6-heptaphthalene 1-fluoro- 2- (3, 5-difluoro-4- (3, 5-difluoro-4-cyanophenyl) phenyl-6- (3-butenyl) naphthalene [Example 30] Preparation of liquid crystal composition (1 )

Preparation of a universal master liquid crystal (Η)

F

It has a wide temperature range and low viscosity, and may also be used by users for the application of the active matrix drive. This (Η) shows a nematic phase at a temperature of 1 1 6. 7 ° C, and its melting point is +1 1 ° c. The physical property value of this composition and the electro-optical characteristics of the liquid crystal element prepared by using this composition are as follows:

Critical value voltage (Vth): 2. 14V dielectric anisotropy (Δε): 4. 8 response time (rr = τ d): 25 · 3m seconds refractive index anisotropy (Δη): 0.090 here , The threshold voltage (V th) and the response time are the values measured in a sealed tank thickness of 6 // m TN at 20 ° C. The response time is the rise time.

88106446.ptc Page 204 528794

(r r) is equal to the fall time (r d) &lt; Secondly, according to the ratio of 80% of the main liquid crystal, the measured value when the compound (Ib-1) of the invention is applied with a voltage. The sample obtained in Example 15

(lb-1) Press 2 0 /. The ratio is added to the above-mentioned main liquid crystal with a wide range of temperature and t liquid crystal is particularly suitable for active matrix drive.

^ ^) In! After standing at 50 t for 20 hours, it was determined to be 97.8C, which was almost unchanged compared with that before heating. In addition, ^ Zixi ^, and Quan were irradiated for 20 hours'. As a result, there was no change in Tn ^. The voltage retention rate of the product is determined. As a result, after the heating, after the heating, the external line and the main liquid crystal (H) are shown to show a sufficiently high value. And ',, one, two,' will (M -1) Filling a groove with a thickness of 45 // m to prepare a liquid crystal element and measuring its electro-optical characteristics' results obtained are as follows: Japanese-Japanese nematic phase upper limit temperature (TN-)): qR fi〇p Dielectric anisotropy (△ ε): threshold voltage (Vth): 4, 6〇

Response time (r): K? 6V

m lL ye ^ 2 4 · 2 m ancient speed: "by Γ 添 i (Ib— &quot; 'It is possible to achieve the same as Κ Κίί shows that the dielectric anisotropy is less than ⑻, and the critical value of the electric second pull main % Degree. Secondly, measure the room temperature of this device and the voltage dynamic matrix drive at 80 ° C. The sub-earths are all very good and can be used for live

528794

[实施 例 3 1] Preparation of liquid crystal composition (2) Second, according to the ratio of 80% of the main liquid crystal, the compound (I b-2) c3h7 of the present invention obtained in Example 15 was used.

(lb-2) adding the above-mentioned main liquid crystal (Η) having a wide temperature range and having a wide temperature range as a low-viscosity liquid crystal particularly suitable for active matrix driving to prepare a liquid crystal composition (M-2) at a ratio of 20%, The measurement results of i (M-2) were obtained, and the electro-optical characteristics measured after the same preparation of the liquid crystal element were as follows: Nematic phase upper limit temperature (TNM): 92.7 ° c Dielectric anisotropy (△ ε): 5. 7

Threshold voltage (Vth): 1.53V Response time (r): 28.0m seconds Therefore, it is known that the dielectric anisotropy of (lb-2) is greater than (H), and the threshold voltage is reduced by 20%. Furthermore, the results of the thermal stability test and the ultraviolet irradiation test performed in the same manner as in the above (M-1)-(M-2) were not found to be changed. In addition, as a result of measuring its voltage holding ratio, it still showed a sufficiently high value during preparation, after heating, and after irradiation with ultraviolet rays. As mentioned above, the compound of general formula (I) is very useful for preparing a ① with a wide nematic phase temperature range, ② shows that the threshold voltage is low, it is possible to achieve low-voltage driving, ③ it is possible to achieve high-speed response, ④ and the voltage It is also sufficiently possible to realize a liquid crystal composition driven by a moving moment.

88106446.ptc Page 206 Case No. 88106446__year ... 年 倏 正 五. Description of the invention (204) [贯 例 3 2] Preparation of liquid crystal composition (3) Secondly, according to the ratio of 80% of the main liquid crystal , The compound (Ic-7) obtained from Example 2 in Example 2 ^ C3H7 528794 91 Λ 1 4

(Jc-7) Adding the above-mentioned main liquid crystal (H) with a wide temperature range and a low viscosity liquid crystal which is particularly suitable for active matrix driving at a ratio of 20% to prepare a crystal composition (M-3), The obtained measurement results of (M-3) and (Tni) and the electro-optical characteristics measured after the same preparation of the liquid crystal element are as follows: V ^ CN: threshold voltage (vth): dielectric anisotropy (△ ε) Refractive index anisotropy (△! 〇 That is, the addition of (Ic-) can increase the nematic phase at 120 ° C -2 ° C 2. 06V 5. 5 0.110 Limit temperature (Tw) is increased by 3 ° np, ,-, ^ v aN-1 / ^ wu 甘 p. Furthermore, this (M-3) was cooled to -60 ° C to crystallize and measured ^ The result was _2 ° C and (H) In comparison, the reduction value reached 13 ° C ~~, and the stable temperature range of the nematic phase expanded by as much as 6 I. == I know that the addition of (Ic-7) increases the dielectric rate. And decrease the criticality. Outside the dagger, the refractive index anisotropy is increased, and the main liquid crystal is used as the reference date to keep it down to suppress 0.02. Next, the room temperature of this device and the voltage retention rate of 801 are measured. Get the voltage retention rate Very good, can be fully used. [Comparative Example 1]

Page 207 528794

In Example 32, the spleen (τ Γ -7, Qierren, replaced the compound of (IC 7) with (R-1)

vy Bu (R-1)

The compound, which has a virtual 4,5 / ^ F alkynyl group was replaced by 1,4-phenylene to add (H), and f prepared / day '/ at the same ratio (20%) as above (HR-i). The nematic upper limit temperature of the composition (T N-1) a 1 in ° r, A m. , Each evening ^ ^. Compared with (M-3), the result is lowered Γμ- ^ Λ The melting point 1 is 5t, which is higher than (M-3). As a result, the temperature range of the &gt; nematic nematic phase is reduced by more than 25 ° C. Example 3 3] Preparation of liquid crystal composition (4) Next, the compound (I d-1) of the present invention obtained in Example 12 was used at a ratio of 80% of the main liquid crystal.

Adding the above-mentioned main liquid crystal (H) having a wide temperature range with a wide temperature range as a low-viscosity liquid crystal at a ratio of 2 Owt%, which is particularly suitable for active matrix driving, to prepare a liquid crystal composition (M-4), and obtaining (M -4) (TNM) measurement results, and the electro-optical characteristics measured after the same preparation of the liquid crystal element are as follows: Ding Bu 1: 9 1. 0 ° C threshold voltage (Vth): 1. 94V dielectric constant difference Squareness (△ ε): 4. 85 Response time (7: r = I * d): 28 · 4m seconds Refractive index anisotropy (△ η): 0.112 Therefore, it is known that due to the addition of (I d- 1) 2 0%, although the maximum nematic temperature

. 社 · 1.4 Revised stomach 528794 Revised case No. 88106446 V. Description of the invention (206) (Tn-i) is lowered, but the response time is not worsened, the threshold is lowered, the voltage is reduced and the refractive index is greatly improved Anisotropy (based on the main liquid crystal (H) as the reference, about 0 · 0 2). Secondly, this composition was left at room temperature for j months, and as a result, no crystal deposition or phase separation was observed. Thus, it is known that (Id_ 丨) ^ the conventional liquid crystal has excellent compatibility. Furthermore, this (丨 b) was cooled to -15 C- to crystallize and the melting point (Tcn) was measured to be 14. [焉 实施 例 3 4] Preparation of liquid crystal composition (5) Secondly, according to the ratio of 80% of the main liquid crystal, a ^ t invention compound (Id-2) will be obtained according to Example 3

F C3H7 -F (id-2)

F is added at the same ratio (20%) to prepare the physical properties of a composition, and the composition / night crystal composition (M_6) is used. The value of this optical characteristic is as follows: Electricity V of the produced liquid crystal element: 8 5. 1 ° C 1. 74V 5. 7 3 1. 1 m second threshold voltage (V th) ·· Dielectric rate difference Squareness (△ ε): Response time (τ r = τ d): Refractive index anisotropy (△ !!): Therefore, compared with (M-4), although 0,107 is lower and refractive index anisotropy A slight decrease, the value of the upper limit temperature of the column phase decreases slightly to further reduce the threshold voltage. / 、 Have the same fast response and [Example 3 5] Preparation of liquid crystal composition (6) Secondly, according to the ratio of 80% of the main liquid crystal, &amp; the original 88106446.ptc obtained in Example 12 528794 V. Description of the invention (207) Compound of the invention (I d-7) Case number 88106446

Amend

Yan, Han 14 Correction I

F (W-7) was added at the same ratio (20%) to prepare ~ the physical property value of the composition, and the composition ~ the liquid crystal composition (M-6) was used. The value of this optical characteristic is as follows: Electricity of the liquid crystal element produced by the object Τνμ: 8 6. 0 ° C 12 ° C 1. 65V 6. 5 0.107

Tc-N: threshold voltage (Vth): dielectric anisotropy (△ £): refractive index anisotropy (Δη): response time (rr = rd): due to addition of (Id-7) compound 2〇 % 8 "Second D is lowered a little ', but it is possible to achieve the upper limit temperature of the disc ^ 7 nematic phase and to achieve a substantially high speed response (0 and (), and Hatsuta UJ · d V) to reduce the threshold voltage. With (Η ) For the sake of beauty, the introduction of the anisotropy of the refractive index ^ Feng Yihan Rishou, has also been greatly improved. L Comparative Example 2] In Examples 3 2 to 35, π c) Xi mustard Inscription, replace the UcJ &gt; compound with (R-2)

F (R-2) = compound, with a structure similar to (IC), (where Qinyl is replaced by 1, "phenyl, which is added in the same phase as above (H) and the ratio of the ratio of preparation to the liquid crystal composition (HR_2) Π—the ratio ⑻ and the electro-optical characteristics are as follows:

88106446.ptc Page 210

I 528794 Year of revision number ... j Revision V. Description of the invention (208) Tn-i · 8 6.0 ° C Threshold voltage (Vth): 1.86V Dielectric anisotropy (Αε): 4.92 Response time ( rr = rd): 2 7 · 0 m seconds Refractive index anisotropy (An): 0.096 Zhengzheng learned that compared with (JU), the response time is faster and the threshold voltage is slightly reduced. However, the upper limit temperature of the nematic phase (τN ι) becomes lower, and the refractive index anisotropy (Δn) also increases slightly. [Effects of the Invention] The fluorine-substituted 2-benzonaphthalene derivative provided according to the present invention has excellent liquid crystallinity and compatibility with a liquid crystal compound or a liquid crystal composition currently in common use. With the addition of this derivative, Arimachi can significantly reduce its threshold voltage while maintaining high-speed responsiveness. It also has a large index anisotropy for its characteristics. In addition, since there is no strong polar group in the molecule, it can be used for applications that are driven by an active matrix. Furthermore, as shown in the examples, it can be easily manufactured industrially, is colorless, and is chemically stable. Therefore, the liquid crystal composition containing the derivative is useful as a practical liquid crystal electrode for liquid crystal displays that require a large temperature range, high-speed response, and low-voltage driving.

88106446.ptc 528794 yi. 5 -t .. ^ 乂 ^ Case No. 88106446_ Year Month _ Correction _ Correction V. Description of the Invention (209) [Example 3 6] Preparation of Liquid Crystal Composition (7) Main Liquid Crystal (H) 90% and compounds of the invention (iatb)

When the 10% liquid crystal composition (Η-7) is prepared, the upper limit temperature of the nematic phase is 11 8 · 6 ° C, and the temperature range of the liquid crystal phase can be expanded by the main liquid crystal (Η). Next, the same liquid crystal element was prepared using the composition, and the characteristic value was measured, and the value was as follows:

Τν-ι: 118. 6 ° C

Critical value voltage (Vth): 2. 04V dielectric anisotropy (△ ε) · 4. 7 refractive index anisotropy (An) · 0.100 Therefore, the addition of the compound (Iatb) of the present invention expands 1 V。 Nematic phase upper limit temperature of the liquid crystal composition ^]), and the threshold voltage (vth) can also be reduced by 0.1 V. Secondly, the voltage retention of this component was measured at room temperature and 80 ° C. As a result, it was found that the voltage retention was very good and showed superior quality. [Example 3 7] Preparation of liquid crystal composition (8) 90% of main liquid crystal (H) and compound (idbm) of the present invention

88106446.ptc Page 212

Chapter 213

88106446.ptc Page 214 Amendment page 528794 Case No. 88106446 V. Description of the invention (212) Month and month correction correction exemption j Example 3 9 Comparative example 3 TN-! (° c) 104. 8 89. 5 Δ £ 9. 9 11.9 Δη 0. 159 0. 144 τ r = τ ά 33. 8 39. 6 As shown in the table above, compared with the composition of Comparative Example 3, the liquid crystal phase temperature range of the liquid crystal composition of Example 3 9 Wider and faster response time. The content of naphthalene and the main uses of Examples 36 to 39 are summarized as follows:

Example number Naphthalene content Main use 36 10% TFT 37 10% STN 38 5 ° / 〇 STN 39 15¾ STN

[Example 40] and [Comparative Example 4] Preparation of liquid crystal composition (11) The following nematic liquid crystal composition was adjusted. CN 7.5% 2Hfr ^ 0 ^ cn 5.4% C〇2-ON 5.4% F n-C5H1r ^^^ C〇2 ^^ »CN η αδ. /. n-C3H7- &lt; ^) ^ C = C2H5 2.2%

CN 8.6% c〇2-CH3 5.4%

• C5H1T • C3

II

88106446.ptc Page 215 Amendment Page 528794 — Case No. 88106446__Year Month Five, Description of the Invention (213) 43% Foreign 乂 〇V »/ 3.2% r ^ y ^ y ^ Qr CH3 12.9% CH3 13.9% r Year In addition, 'Comparative Example 4 replaced the compound (Icjbm) of the present invention with (R-3) to prepare a liquid crystal composition (Comparative Example 4), the physical properties of the composition, and the same liquid crystal element was prepared using the composition, and This characteristic value was measured as follows: Example 4 0 Comparative Example 4 V! (° c) 108. 3 99. 4 Vth (V) 1. 58 1. 51 Δ ε 10. 6 10. 5 Δη 0. 151 0. 144 τ r = τ d 34. 8 35. 3 Table 5 Example 4 0 and Comparative Example 4 As shown in the above table, when compared with the composition of Comparative Example 4, Example 4 0 can be found The liquid crystal composition has a wide liquid crystal phase temperature range. [Example 4 1] Preparation of liquid crystal composition (2) The compound (I dbb) of the present invention was contained, and the following liquid crystal composition was adjusted.

i-C3H

(Idbb) 30%

Page 216 2001.07. 05.216 Revised page 528794 Case No. 8810644R V. Description of the invention (214)

22.5%

F 22.5% r, ~ C3H

The composition and the refractive index of the tertiary N-1: Tc-N: 6¾ threshold dielectric constant response are measured. Therefore, the voltage value, the response is good, and the stability is a liquid crystal material. [Example 4 2] Contains the liquid crystal group 98.1 ° C-70 t: 1. 79V 6. 0 29m seconds 0.118 15% 10% physical property value and the same liquid crystal element prepared by using the composition. The property value is as follows: The following: Voltage (Vth): anisotropy (△ ε): interval (τ r = τ d): anisotropy (△ η): liquid crystal composition with the compound (I dbb) of the present invention, its critical application The balance of characteristics such as time and liquid crystal display elements is a wide range of applications. In addition, since the liquid crystal phase is very superior at a low temperature ', it can be seen that the liquid crystal material of the present invention is also very compatible with other materials. Preparation of the liquid crystal composition (1 3) The compounds (Idbb), (Idbc), and (Icbb) were adjusted, and the resultant was adjusted.

88106446.ptc Page 217 528794

88106446.ptc Page 218

Amendment page 528794 Case number 88106446 91. 5, [4 years in advance 91 5. 1 Amendment page V. Description of invention (216)

Tn-1: 8 9. 7 ° C TON ·· -70 ° C threshold voltage (Vth): 1. 59V dielectric anisotropy (△ ε): 7. 7 response time (τ r = τ d): 4 4 m second refractive index anisotropy (An): 0.106 The liquid crystal composition containing the compound (Idbb), (I dbc), (Icbb) of the present invention has a low threshold voltage (V th) Can make display elements. The liquid crystal composition is also superior in liquid crystal phase stability at low temperatures. Reference [Example 43] Preparation of liquid crystal composition (14) The compounds (Idbb), (Idbc), (Icba), and (Icbb) of the present invention were contained, and the following liquid crystal composition was adjusted.

15%

10% 10% 15%

Plant 10% physical property value of the composition and use the composition to prepare the same liquid crystal element, and determine the characteristic value, the value is as follows: surface 88106446.ptc page 219 528794% B. 14 amendment page_case number 88106446 _Year 4 Amendment the next day V. Invention description (217)

Tn-1 · 9 4. 9 ° C ΤΝ ·-70 〇C threshold voltage (Vth): 1. 75V dielectric anisotropy (△ ε): 8. 7 response time (rr = 7: d ): 30 m second refractive index anisotropy (△ !!): 0. 149 Liquid crystal composition containing the compound (Idbb), (Idbc), (Icba), (Icbb) of the present invention. A highly effective liquid crystal composition can achieve very good results. In order to increase the liquid crystal material with the previous refractive index anisotropy, it is mainly used for long conjugated compounds. However, in the case where the crystallinity is better, the low temperature stability of the composition is often poor. However, the amount cannot be added sufficiently, and the refractive index anisotropy cannot be sufficiently increased. Therefore, using the liquid crystal composition of the liquid crystal material of the present invention, a total of only 60% of the naphthalene-based compound is used, and it can have a low temperature limit of -70 ° C and a low liquid crystal phase. [Example 44] Preparation of liquid crystal composition (1 5) The compound (I bae) of the present invention was contained, and the following liquid crystal composition was adjusted.

88106446.ptc Page 220 91 5. 14 Revised Page 528794 Case No. 88106446 V. Description of Invention (218)

F Menyang Plant ίο% The physical property value of the composition and the same liquid crystal element prepared by using the composition, and the characteristic value is measured, and the value is as follows:

TNM: 8 5. 9 X:

TC_N: -70 ° C

Critical value voltage (Vth): 1. 76V dielectric anisotropy (△ ε): 5.8 response time (τ r = r d): 5 4 m seconds refractive index anisotropy (Λη): 0.113

The liquid crystal composition containing two types of compounds having different alkyl chains of the compound (Ibae) of the present invention has low temperature stability of the liquid crystal phase even if it is only added in a total amount of 80%. In addition, the characteristics of the liquid crystal display device can be well balanced and superior.

88106446.ptc page 221 528794 case number 88106446

88106446.ptc Page 222 Correction page

Claims (1)

^ 28794 Case No. 88106446 Λ_ Name Amendment Amendment 6. Scope of patent application 1 · A compound of a naphthalene derivative represented by formula (I), wherein x ° X3 (0 X1 Ra represents an alkyl group, alkoxy group, alkoxyalkyl group, alkenyl group, or alkenyl group having 1 to 20 carbon atoms, and these groups may have an alkoxy group having 1 to 7 carbon atoms Or a substituent of 1 to 7 fluorine atoms; a and b are 0 or 1 and satisfy a &gt;b; ring A and ring B each independently represent trans 1,4-cyclohexyl, and may be substituted with more than one 1,4-phenylene and pyrimidine-2,5-diyl of fluorine atom; La ALb each represents -CH2CH2-, -CH2CH2CH2CH2-, CH = CH-, -CH = CHCH2CH2-, -CH2CH2CH = CH- , -CH (CH3) CH2, oco -CH2CH (CH3), -cf = cf-, cf2o-, -ocf2-, -coo-, or single bond; X1 ~ X6 each independently represent a hydrogen atom or a fluorine atom, but X2 It is not an atom at the same time as X4 or X3 and X6; Za represents a gas atom, a chlorine atom, a trifluorofluorenyloxy group, and may have an alkoxy group having 1 to 7 carbon atoms or a substituent having 1 to 7 fluorine atoms. C1-C20 alkyl, alkoxy, alkenyl, alkenyl, or a group represented by general formula (Ila) or (lib); C V-Z5 (Jla) Z &quot; (lib) where Lc and! / Are separately indicated -CH2CH2-, -CH2CH2CH2CH2--CH = CH-, -CH = CHCH2CH2-, CH2CH2CΗ = CH-, 88] 06446; ptc p.223 528794 -SS_J81〇6446 6. Patent application scope-ch (ch3) ch2 -COO-, -0C0 • CH2CH (CH3), -CF CF-, -CF20-, -〇CF2-, Ring C and ring D each have a single primary 4 early bond, and the m of the fluorine atom on the above represents an anti-u-cyclohexyl group, which can be substituted with 1 ~ 2. Benzene, 4 ~ phenylene and pyrimidine-2,5-diyl, ·, cyano,: difluoro atom, chlorine atom, molybdenum atom, androgen atom, hydrogen atom C00R &gt; &quot; ^, -0CN, —R ', -OR ,, -0C0R, or an alkyl or alkoxy group or an alkenyl group or alkenyloxy group of the original di-table number of carbon atoms Ϊ to 20 or 反' t t π ^ #, etc. The group may have a carbon number of 1 to II, a substituent of Sm group, fluorenyloxy group, or alkoxycarbonyl group, or more, and more hydrogen atoms contained in iI may be substituted by one or more fluorine atoms. In the case where asymmetric carbon atoms are generated or divided, the photon / tongue property may be used or it may become a racemic form, but with the following conditions: M Fang Xi: When the base shown in the formula (I 13), b Is 0, if 々 is the general formula (IIb)… is 0, and if Z3 represents an atom, a chlorine atom, and trifluoro: ί has an alkoxy group having 1 to 7 carbon atoms or 1 to 7 oxygen atoms Oxygen radicals a, an alkyl group having 1 to 2 carbon atoms, an alkyloxy group, a dilute group, a dilute group 2) If Za is a group represented by the general formula (I Ia), the ring c represents a substituted group No.1, 4-Extending it, 7b edition today-today shield workers Buranyuan When 4 is the basic group, and Zb represents a fluorine atom, a gas atom, and a trialkyl group may have an alkyl or alkoxy group having a fluorine atom substituent, Lc represents milk -CH2CH2CH2CH2-, -CH = CH-, -CH = CHCH2CH2-, ', CH2CH2CH = CH-, one CH (CH3) CH2, -ch2ch (ch3), -CF = cf, one cf20-, or one 0Cf2-, and / or at least two of x〗 ~ χ6,丨 clothing not fluorine original 528794 _ case number 88106446_ year month amendment _ six, the scope of patent application 3) if Za represents alkyl or alkoxy, at least one of X1 ~ X6 represents a fluorine atom 'and / Or B (: represents -〇) 12〇} 12〇1] 2〇112-, _〇? :::::: 〇?-, -0? 2〇- or ocf2 ~; 4) if Za represents a fluorine atom Or a gas atom, La represents a single bond, and if ring A represents a 1,4-phenylene group which may have a fluorine atom substituent, b is 0 or b is 1, and Lb represents a single bond; and 5) if a When = b = 0, X1 represents a fluorine atom, and X2 to X6 each represents a hydrogen atom; if Le represents a single bond, Zb represents a fluorine atom, a gas atom, a hydrogen atom, a trifluoromethoxy group, an alkenyl group, and an alkenyl group , Cyano, or cyano. 2. As for the compound in the first scope of the patent application, where a = b = 1. 3. For example, the compound in the first item of the patent application scope, wherein a = 1, b = 0, and 0 is selected from the group consisting of fluorine atom, chlorine atom, trifluorofluorenyloxy group, and may have an alkoxy group having 1 to 7 carbon atoms. Or a substituent of 1 to 7 fluorine atoms having an alkyl group, alkoxy group, alkenyl group or alkenyl group having 1 to 20 carbon atoms. 4 · The compound according to item 1 of the scope of patent application, wherein a = 1, b = 0, and 28 is represented by the general formula (Ila). 5. The compound according to item 1 of the patent application scope, wherein a = b = 0, and Za is represented by the general formula (Ila). 6 · The compound according to item 1 of the scope of patent application, wherein a = b = 0, and Za is represented by the general formula (lib). 7. The compound according to item 1 of the scope of patent application, wherein La, Lb, Lc, and Ld are each independently selected from -CH2CH2- or a single bond. 8. The compound according to item 1 in the scope of patent application, wherein ring A is selected from trans 1,4-cyclohexyl, 1,4-phenylene, 2-fluoro_1,4-phenylene, 2, 6 -two 88106446.ptc Page 225 528794 Case No. 88106446 Amendment VI. Scope of Patent Application Fluoro-1,4-phenylene, or trans-decahydro-2,6-diyl. 9. The compound according to item 1 of the scope of patent application, wherein ring B is trans 1,4-cyclo'cyclohexyl. · 10. The compound according to item 1 in the scope of patent application, wherein ring C and ring D are each independently selected from 1,4-phenylene, 2-fluoro-1,4-phenylene and 3-fluoro4 -Phenylene, 2,3-difluoro-1,4-phenylene, or 3,5-difluoro-1,4-phenylene. 1 1. The compound according to item 1 of the scope of patent application, wherein Za is selected from the group consisting of alkenyl groups having 4 to 12 carbon atoms or alkenyl groups having 3 to 12 carbon atoms which may have a substituent having 1 to 3 fluorine atoms. Base. 1 2. The compound according to item 1 of the scope of patent application, wherein Za is selected from the group consisting of an alkyl group or an alkoxy group having 1 to 12 carbon atoms which may have a substituent having 1 to 7 fluorine atoms. 1 3. The compound according to item 12 of the scope of patent application, wherein Za is trifluorofluorenyloxy. 1 4. The compound according to item 1 of the scope of patent application, wherein X1 is a fluorine atom. 15. The compound according to item 14 of the scope of patent application, wherein X2 is a fluorine atom. 1 6. The compound according to item 2 of the patent application, in which X1 and X2 are both fluorine atoms. 1 7. The compound according to item 3 of the patent application, in which X1 and X2 are both fluorine atoms. 1 8. A liquid crystal composition, comprising one or two or more 88106446.ptc Page 226 528794 Case No. 88I0b446 Revised on May 26, 2006. The scope of application for a patent, such as the first scope of the patent application, contains 5 to 80%. Furthermore, the compound contains one or two or more Derived from phenyl phenyl sulfonate, phenyl cyclohexane sulfonate, biphenyl-4-yl cyclohexane derivate, phenyl cyclohexyloxybenzoate derivate, cyclohexyl phenyl hydrazone Acid phenyl ester derivative, cyclohexyl benzoate cyclohexyl derivative, biphenyl derivative, cyclohexyl derivative, bitriphenyl derivative, dicyclohexane derivative, 4-cyclohexyl biphenyl derivative, 4 -Stupid bicyclohexane derivative, ditricyclohexane derivative, 1,2-biscyclohexylethane derivative, 1,2-diphenylethane derivative, 1,2-diphenylacetylene derivative, (2-cyclohexylethyl) benzene derivative, 4-phenethylbicyclohexane derivative, 4- (2-cyclohexylethyl) biphenyl derivative, 1- (4-phenyl) cyclohexyl-2 -Cyclohexylethane derivative, 1- (4-cyclohexylphenyl) -2-phenylacetylene derivative, phenyl 17 dense bite derivative, (4-biphenyl-4-yl) u dense bite derivative All Optional compounds, the content rate of 20% ~ 9 5%. 19. The liquid crystal composition according to item 18 of the scope of patent application, wherein the liquid crystal composition is used as a driver of the active matrix. 20. The liquid crystal composition according to item 18 of the scope of patent application, wherein the liquid crystal composition is used as a constituent element of a liquid crystal display element. 2 1. The liquid crystal composition according to item 20 of the patent application, wherein the liquid crystal display element is used as a driver of an active matrix. 88106446.ptc Page 227