| 摘要 |
<p>#CMT# #/CMT# 4-[(3,5-Difluoro-4-trifluoromethyl-phenoxy)-difluoro-methyl]-3,5,2'-trifluoro-biphenyl compounds (I), are new. #CMT# : #/CMT# 4-[(3,5-Difluoro-4-trifluoromethyl-phenoxy)-difluoro-methyl]-3,5,2'-trifluoro-biphenyl compounds of formula (I), are new. A1 : 1,4-phenylene, which is optionally up to 4 times substituted by halo, CN, CH 3, CHF 2, CH 2F, OCH 3, OCF 3or OCHF 2and 1-2 CH-groups (optionally substituted by N), cyclohexane-1,4-diyl or cyclohexene-1,4-diyl, in which each optionally 1-2 CH 2groups can be substituted by O or S and/or H or F, bicyclo[1.1.1]pentane-1,3-diyl, bicyclo[2.2.2]octane-1,4-diyl, spiro[3.3]heptan-2,6-diyl, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, 2,5-thiophenediyl or 2,5-selenophenediyl; Z1 : a single bond, CF 2O, CH 2CH 2, CF 2CH 2, CF 2CF 2, CFHCFH, CFHCH 2, (CO)O, CH 2O, C=C, CH=CH, CF=CH or CF=CF, where unsymmetrical connecting links can be oriented in both possible directions; and R1 : 1-15C unsubstituted alkyl, in which rest one or more CH 2groups are replaced by -CC-, -CH=CH-, -CF=CF-, -CF=CH-, -CH=CF-, -(CO)O-, -O(CO)-, -(CO)- or -O- in such a way that O atoms are not linked directly to each other, H, F, Cl, Br, CN, CF 3, OCF 3, SCN, NCS or SF 5. Independent claims are included for: (1) the preparation of (I); (2) a liquid-crystalline medium comprising (I); and (3) an electro-optical display device comprising the liquid crystalline medium. #CMT#[Image]#/CMT# #CMT#USE : #/CMT# (I) are useful in a liquid crystalline medium and an electro-optical display (all claimed). #CMT#ADVANTAGE : #/CMT# (I) exhibit high dielectric anisotropy, optical anisotropy and high clearing point. #CMT#ORGANIC CHEMISTRY : #/CMT# Preparation (Claimed): Preparation of (I) comprises reacting two reactants of formula (A) and (B1) in the presence of a suitable transition metal catalyst.X1, X2 = -B(OH) 2, boronic acid ester, boronate salt, Cl, Br, I or -O(SO 2)CF 3. Preferred Components: The liquid-crystalline medium further contains substituted biphenyl compounds of formula (II) or (III). The electro-optical display device operates completely or partially in the field of liquid crystalline blue phase. A2, A3 : p-xylene, 2-fluoro-1,4-dimethyl-benzene, 1,3-difluoro-2,5-dimethyl-benzene, 2,5-dimethyl-pyridine, 2,5-dimethyl-pyrimidine, 2,5-dimethyl-[1,3]dioxane, 2-fluoro-1,4-dimethyl-benzene or 1,4-dimethyl-cyclohexane; Z2, Z3 : Z1; X1 : F, Cl, CN, alkyl, alkenyl, alkenyloxy, alkoxyalkyl or 1-3C alkoxy, which is substituted by F; and L1-L4 : H or F. #CMT#[Image]#/CMT# #CMT#[Image]#/CMT# #CMT#DEFINITIONS : #/CMT# Preferred Definitions: Z1 : single bond; A1 : p-xylene, 2-fluoro-1,4-dimethyl-benzene, 1,3-difluoro-2,5-dimethyl-benzene, 1,4-dimethyl-cyclohexane, 2,5-dimethyl-tetrahydro-pyran, 2,5-dimethyl-[1,3]dioxane, 2,5-dimethyl-pyridine, 2,5-dimethyl-pyrimidine, 2,5-dimethyl-thiophene or 2,5-dimethyl-selenophene; and R1 : linear 3C alkyl. #CMT#SPECIFIC COMPOUNDS : #/CMT# 10 Compounds (I) are disclosed e.g. 2-{4'-[(3,5-difluoro-4-trifluoromethyl-phenoxy)-difluoromethyl]-2,3',5'-trifluoro-biphenyl-4-yl}-5-propyl-tetrahydropyran of formula (Ia), 2-{4'-[(3,5-difluoro-4-trifluoromethyl-phenoxy)-difluoro-methyl]-2,3',5'-trifluoro-biphenyl-4-yl}-5-ethyl-tetrahydropyran, 2-{4'-[(3,5-difluoro-4-trifluoromethyl-phenoxy)-difluoromethyl]-2,3',5'-trifluoro-biphenyl-4-yl}-5-pentyl-tetrahydropyran, 5-butyl-2-{4'-[(3,5-difluoro-4-trifluoromethyl-phenoxy)difluoromethyl]-2,3',5'-trifluoro-biphenyl-4-yl}-tetrahydropyran and 2-{4'-[(3,5-difluoro-4-trifluoromethyl-phenoxy)-difluoro-methyl]-2,3',5'-trifluoro-biphenyl-4-yl}-5-heptyl-tetrahydropyran. #CMT#[Image]#/CMT# #CMT#EXAMPLE : #/CMT# A mixture of trifluoromethanesulfonic acid-2-fluoro-4-(trans-5-propyl-tetrahydropyran-2-yl)-phenyl ester (10 g) and 2-{4-[(3,5-difluoro-4-trifluoromethyl-phenoxy)-difluoromethyl]-3,5-difluorophenyl}-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (14.3 g), tetrakis(triphenylphosphine)-palladium(0) (1.5 g) and 2 N sodium carbonate solution (30 ml) in toluene/ethanol (1:1) (100 ml) was heated for 20 hours. After cooling, the organic phase was separated and the aqueous phase was extracted with methyl tert-butyl ether. The combined organic phases were washed with water. The solution was dried with sodium sulfate and completely concentrated to obtain 2-{4'-[(3,5-difluoro-4-trifluoromethyl-phenoxy)-difluoromethyl]-2,3',5'-trifluoro-biphenyl-4-yl}-5-propyl-tetrahydropyran.</p> |
