CN1141645A - 可聚合的手性化合物和它们的用途 - Google Patents
可聚合的手性化合物和它们的用途 Download PDFInfo
- Publication number
- CN1141645A CN1141645A CN94194817A CN94194817A CN1141645A CN 1141645 A CN1141645 A CN 1141645A CN 94194817 A CN94194817 A CN 94194817A CN 94194817 A CN94194817 A CN 94194817A CN 1141645 A CN1141645 A CN 1141645A
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- Prior art keywords
- compound
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- chiral
- mesomorphic
- independently
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 26
- 125000006850 spacer group Chemical group 0.000 claims abstract description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol group Chemical group [C@@H]1(CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C)[C@H](C)CCCC(C)C HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims description 10
- 239000002019 doping agent Substances 0.000 claims description 5
- 239000004973 liquid crystal related substance Substances 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 230000003098 cholesteric effect Effects 0.000 abstract description 3
- 239000004988 Nematic liquid crystal Substances 0.000 abstract description 2
- 239000003086 colorant Substances 0.000 abstract description 2
- 238000002360 preparation method Methods 0.000 abstract description 2
- 239000004986 Cholesteric liquid crystals (ChLC) Substances 0.000 abstract 1
- 150000003254 radicals Chemical class 0.000 description 16
- 150000001336 alkenes Chemical class 0.000 description 14
- 239000012071 phase Substances 0.000 description 12
- 238000000034 method Methods 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 239000001301 oxygen Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 125000004494 ethyl ester group Chemical group 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 229960002920 sorbitol Drugs 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 150000001720 carbohydrates Chemical class 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 150000002334 glycols Chemical class 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000000967 suction filtration Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VQKFNUFAXTZWDK-UHFFFAOYSA-N alpha-methylfuran Natural products CC1=CC=CO1 VQKFNUFAXTZWDK-UHFFFAOYSA-N 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 239000003205 fragrance Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 235000015320 potassium carbonate Nutrition 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 150000003431 steroids Chemical class 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- JTGCXYYDAVPSFD-UHFFFAOYSA-N 4-(4-hydroxyphenyl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=C(O)C=C1 JTGCXYYDAVPSFD-UHFFFAOYSA-N 0.000 description 1
- 241000819038 Chichester Species 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- -1 acrylic compound Chemical class 0.000 description 1
- 125000001118 alkylidene group Chemical group 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 230000006399 behavior Effects 0.000 description 1
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000002983 circular dichroism Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- YSAVZVORKRDODB-PHDIDXHHSA-N diethyl (2r,3r)-2,3-dihydroxybutanedioate Chemical compound CCOC(=O)[C@H](O)[C@@H](O)C(=O)OCC YSAVZVORKRDODB-PHDIDXHHSA-N 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 150000002402 hexoses Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 150000002972 pentoses Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 235000007715 potassium iodide Nutrition 0.000 description 1
- 229960004839 potassium iodide Drugs 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 230000003637 steroidlike Effects 0.000 description 1
- 125000003011 styrenyl group Chemical class [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
Classifications
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- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/84—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring
- C07C69/92—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring with etherified hydroxyl groups
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- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/94—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of polycyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of six-membered aromatic rings
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/26—Esters containing oxygen in addition to the carboxy oxygen
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- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
- C09K19/20—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers
- C09K19/2007—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers the chain containing -COO- or -OCO- groups
- C09K19/2021—Compounds containing at least one asymmetric carbon atom
- C09K19/2028—Compounds containing at least one asymmetric carbon atom containing additionally a linking group other than -COO- or -OCO-, e.g. -CH2-CH2-, -CH=CH-, -C=C-; containing at least one additional carbon atom in the chain containing -COO- or -OCO- groups, e.g. -COO-CH*-CH3
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- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
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- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
- C09K19/3066—Cyclohexane rings in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers
- C09K19/3068—Cyclohexane rings in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers chain containing -COO- or -OCO- groups
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- C09K19/322—Compounds containing a naphthalene ring or a completely or partially hydrogenated naphthalene ring
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- C09K19/06—Non-steroidal liquid crystal compounds
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- C09K19/3441—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom
- C09K19/345—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom the heterocyclic ring being a six-membered aromatic ring containing two nitrogen atoms
- C09K19/3458—Uncondensed pyrimidines
- C09K19/3463—Pyrimidine with a carbon chain containing at least one asymmetric carbon atom, i.e. optically active pyrimidines
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- C09K19/3441—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom
- C09K19/345—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom the heterocyclic ring being a six-membered aromatic ring containing two nitrogen atoms
- C09K19/3458—Uncondensed pyrimidines
- C09K19/3469—Pyrimidine with a specific end-group other than alkyl, alkoxy or -C*-
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- C09K19/3491—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having sulfur as hetero atom
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- C09K2019/0444—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group
- C09K2019/0448—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group the end chain group being a polymerizable end group, e.g. -Sp-P or acrylate
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- C09K19/32—Non-steroidal liquid crystal compounds containing condensed ring systems, i.e. fused, bridged or spiro ring systems
- C09K19/322—Compounds containing a naphthalene ring or a completely or partially hydrogenated naphthalene ring
- C09K2019/323—Compounds containing a naphthalene ring or a completely or partially hydrogenated naphthalene ring containing a binaphthyl
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- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3402—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
- C09K19/3405—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom the heterocyclic ring being a five-membered ring
- C09K2019/3408—Five-membered ring with oxygen(s) in fused, bridged or spiro ring systems
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Abstract
本发明涉及可聚合的、手性的化合物，它含有至少一个二价或多价手性基团、至少一个可聚合基团、至少一个间隔基团和至少一个介晶基团，和涉及它们在制备胆甾型网络时作为可聚合的、手性的掺杂剂的用途。该新型化合物适合用于电光显示器或作为向列型或胆甾型液晶的手性掺杂剂、来生产能反射颜色的层。
Description
已知在形状上各向异性的分子在受热时会形成液晶相(称为介晶相)。各相的区别一方面在于分子的主要部分的空间排列和另一方面在于就长轴而言的分子排列(G.W.Gray，P.A.Winsor，Liquid crystals和Plasticcrystals，Ellis Horwood Limited，Chichester，1974)。向列型液晶相突出表现在：因各长分子轴平行排齐而使得仅仅单线远程有序。在组成向列相的分子是手性的前提条件下，形成胆甾相，其中分子的长轴形成与它垂直的螺旋式超结构(H.Baessler，Festkperprobleme XI，1971)。手性结构部分可以存在于液晶分子本身或作为掺杂剂加入到向列相中。通过掺杂产生的相称为诱导胆甾相。这一现象首先在胆甾醇衍生物上研究发现(H.Baessler，M.M.Labes，.J.Chem.Phys.52(1970)631；H.Baessler，T.M.Laronge，M.M.Labes.J.Chem.Phys.51(1969)3213；H.Finkelmann，H.Stegemeyer，Z.Naturforschg.28a(1973)799)。胆甾相的诱导也可通过添加其它本身不是液晶的手性物质来实现(H.Stegemeyer，K.J.Mainusch，Naturwiss.58(1971)599；H.Finkelmann，H.Stegemeyer，Ber.Bunsenges.Phys.Chem.78(1974)869)。
胆甾相具有突出的光学性能：由胆甾层内的圆偏振光的选择性反射引起的大的旋光性和显著的圆振二向色性。根据视角所观察到的不同颜色取决于螺旋式超结构的螺距，它本身取决于手性组分的扭转能。螺距和胆甾层的选择性反射光的波长范围能够改变，尤其通过改变手性掺杂剂的浓度(J.E.Adams，W.E.L.Haas，Mol.Cryst.Liq.Cryst.16(1972)33)。此类胆甾体系为实际应用提供了有益的机会。因此，在胆甾相中排序(alignment)后向内消旋的丙烯酸酯中引入手性结构部分以及光致交联反应能够得到稳定的、着色的网络，但其中的手性组分的浓度不能被改变(G.Galli，M.Laus，A.Angeloni，Makromol.Chem.187(1986)289)。另外，不能交联的手性化合物与光致交联后的胆甾型丙烯酸酯混合能够得到着色的聚合物(I.Heynderickx，D.J.Broer，Mol.Cryst.Liq.Cryst.203(1991)113)，但仍然含有妨碍应用的挥发性成分。
本发明的目的是提供新型的手性化合物，它首先具有高的扭转能，其次能够按任何所需浓度以稳定方式引入胆甾相中，而不会从胆甾相中扩散出去或结晶出来。
我们发现由可聚合的手性化合物可以实现这一目的。
所以，本发明涉及可聚合的、手性的化合物，它含有至少一个二价或多价手性基团、至少一个可聚合基团、至少一个间隔基团和至少一个介晶基团，和涉及它们在制备胆甾型网络时作为可聚合的、手性的掺杂剂用途。
可聚合基团尤其是乙烯基，它们例如存在于丙烯酸化合物、乙烯基醚或苯乙烯衍生物中。环氧化合物也是合适的。
适合于本新型化合物的手性基团尤其是从糖类，来自联苯或联萘系的双官能或多官能化合物，旋光性乙二醇类、二醇或氨基酸。
间隔基和介晶基是通常为此目的使用的基团。
新型化合物所必需的这些基团是通过桥连基相互连接的，如O、COO、OCO、CONH、NHCO、CON(R)、N(R)CO或直接的键。
特别地，本发明提供结构式I的化合物
(Z-Y-A-Y-M-Y-)nX I，其中，在每一种情况下相互独立地，A 是间隔基，M 是介晶基，Y 是直接的键，O，S，COO，OCO，CON(R)或N(R)CO，Z 是可聚合基团，n 是2-6中的数，X 是手性基团 和R 是C1-C4烷基或氢。
间隔基A可以是为此目的所已知的任何基团；间隔基通常通过酯基或醚基或直接的键连接于X。间隔基一般含有2-30个、优选2-12个碳原子，而且在链上可以插入例如O、S、NH或NCH3。间隔基链的可能的取代基是氟、氯、溴、氰基、甲基或乙基。
代表性的间隔基的例子是：(CH2)p，(CH2CH2O)mCH2CH2，CH2CH2SCH2CH2，CH2CH2NHCH2CH2，其中m是1-3和p是1-12。
基团M同样可以是已知的介晶基。特别合适的是含有环脂族、芳族或杂芳族基团的基团。介晶基团尤其满足结构式II
(-T-Y1)r-T II其中，每一个T独立地是亚环烷基，芳族基或杂芳族基，每一个Y1独立地是O，COO，OCO，CH2O，OCH2，CH＝N，N＝CH或直接的键，和r 是0-3。r 优选是0或1。T 一般是非芳族或芳族、碳环族或杂环族环体系，它是未被取代的或被氟、氯、溴、氰基、羟基或硝基取代，并且例如符合以下基本结构：
特别优选的介晶基团例如是：
或
结构式I中的n优选是2或3，尤其是2。
在手性基团X当中，特别优选的是从糖类，联苯或联萘衍生物或旋光性乙二醇类或二醇衍生而来的基团。在糖类的情况下，可特别提及戊糖和己糖及它们的衍生物。
各X基团的例子是：
其中L是C1-C4烷基，C1-C4烷氧基，卤素，COOR，OCOR，CONHR或NHCOR，这里R如上所定义。
特别优选的，例如是：
旋光性乙二醇类或其衍生物例如对应于以下结构式：
其中B1和B2相互独立地是C1-C4烷基，它可以被羟基取代和插入-O-，或者是苯基或取代的或未取代的羧基，和这些基团中的一个可以是氢，在相同基团B1和B2的情况下，排除R，S构型。
此类基团B1和B2例如分别是：CO2CH3，CO2CH2CH3，CO2(CH2)2CH3，CO2(CH2)3CH3，CO2CH(CH3)2，CO2C(CH3)3或-CH(OH)CH2(OH)。合适的还有具有以下结构的特定的双官能手性基团：
优选的基团Z的例子是：其中R如上所定义。
根据本发明的单元Z-Y-A-Y-M-Y(其中Z、Y、A和M如上所定义)能够由一般来说已知的合成方法获得，例如按照DE-A 3917196中描述的方法。
手性结构部分能够通过商业途径获得，因而是易得的。
本新型化合物特别适合用于光电显示元件或作为向列型或胆甾型液晶的手性掺杂剂，来生产能反射颜色的层。
实施例1
2，5-双[4’-(2-丙烯酰氧基乙氧基)联苯基-4-羰氧基]-1，4；3，6-二脱水-D-山梨糖醇a 4’-羟乙氧基联苯基-4-羧酸乙酯
将72.6g(0.3mol)4’-羟基联苯基-4-羧酸乙酯溶于225ml绝对二甲基甲酰胺中，添加45.5g(0.33mol)碳酸钾和3.0g碘化钾。然后添加26.57g(0.33mol)2-氯乙醇，混合物在100℃下加热5小时。在混合物于室温下搅拌过夜后，添加另外的22.77g(0.17mol)碳酸钾和13.3g(0.17mol)2-氯乙醇。混合物在100℃下加热15小时，冷却并在水中沉淀。固体残余物用水洗涤至中性并干燥。湿的产物能够立即进一步反应。
产率：123g湿产物，m.p.(纯物质)128-129℃。b 4’-羟乙氧基联苯基-4-羧酸
将123g(约0.3mol)湿的4’-羟乙氧基联苯基-4-羧酸乙酯溶于258ml乙醇中，添加67.22g(0.6mol)50％浓度的KOH溶液。混合物回流1小时，冷却，过滤出残余物，用乙醇洗涤并抽干。粗产物在水中搅拌，用稀盐酸酸化。抽滤产物，用水洗涤至中性并干燥。
产率：68.0g(约等于88％)，m.p.155℃。c 4’-(2-丙烯酰氧基乙氧基)联苯基-4-羧酸
将38.7g(0.15mol)4’-羟乙氧基联苯基-4-羧酸溶于220ml的1，1，1-三氯乙烷中，添加54.0g(0.75mol)新近蒸馏过的丙烯酸和0.5g氢醌。加入10.0g对甲苯磺酸，混合物在水分离器上回流4小时。然后再添加54.0g(0.75mol)新蒸馏过的丙烯酸，混合物被加热3.5小时一直到全部溶解。冷却混合物，抽滤残余物，用1，1，1-三氯乙烷洗涤，随后与叔丁基甲基醚和水搅拌在一起。抽滤固体残余物，用叔丁基甲基醚洗涤，干燥并从1.4l乙酸乙酯重结晶。
产率：19.0g(约等于41％)。d 丙烯酸2-(4’-氯羰基联苯基-4-基氧基)乙基酯
将9.36g(0.03mol)4’-(2-丙烯酰氧基乙氧基)联苯基-4-羧酸引入25ml草酰氯中，添加一滴二甲基甲酰胺。滴一小滴2，6-二叔丁基甲基酚作为自由基抑制剂，然后反应混合物在40 50℃下加热35分钟。过量的草酰氯随后通过在水泵真空中蒸馏被除去，剩下的油状残余物在油泵真空中干燥过夜。产物可以直接作进一步处理。
产率：10.1g(约等于99％)。e 2，5-双[4’-(2-丙烯酰氧基乙氧基)联苯基-4-羰氧基]-1，4；3，6-二脱水-D-山梨糖醇
将1.99g(0.014mol)1，4；3，6-二脱水-D-山梨糖醇溶于50ml绝对二氯甲烷中，然后添加2.37g(0.03mol)绝对吡啶和一小滴2，6-二叔丁基甲基酚，随后在0-5℃下将9.93g(0.03mol)丙烯酸2-(4’-氯羰基联苯基-4-基氧基)乙基酯溶于20ml绝对二氯乙烷中的溶液滴加进去。混合物在温热下搅拌过夜，然后添加水和小量稀盐酸，混合物用乙醚萃取几次。合并的有机相用水洗涤，用硫酸钠干燥，以及除去溶剂。产物通过柱色谱(硅胶，洗脱液∶甲苯/乙酸乙酯8∶2)提纯。
产率：0.91g(约等于9％)，m.p.＞175℃。1H-NMR(200MHz，CDCl3)：δ＝4.11(d，J＝6.3Hz，2H，-CH2-，环H)，4.15(m，2H，-CH2-，环H)，4.25(t，J＝6Hz，4H，-CH2-OAr)，4.55(t，J＝6Hz，4H，-CH2-OCOR)，4.75(d，J＝6Hz，1H，桥H).5.13(t，J＝6Hz，1H，桥H)，5.45(q，J＝6 Hz，1H，环H)，5.55(m，1H，环H)，5.88(d，J＝10.6Hz.2H.烯H)，6.20(dd，J＝17Hz，J′＝10.6Hz，2H，烯H)，7.0(d，J＝8.6Hz，4H，芳香H)，7.5-7.7(m，8H，芳香H)，8.06(d，J＝8.6Hz，2H，芳香H)，8.13(d，J＝8.6Hz，2H，芳香H).
实施例2
2，5-双[4’-(2-丙烯酰氧基乙氧基)苯基-4-羰氧基]-1，4；3，6-二脱水-D-山梨糖醇
使用4-羟基苯甲酸乙酯，按类似于实施例1中的方法制备该化合物。产率：1.24g(约等于16％)，m.p.＞156℃。1H-NMR(200 MHz，CDCl3)：δ＝4.05(d，J＝5.7Hz，2H，-CH2-，环H)，4.12(m，2H，-CH2-，环H)，4.24(t，J＝6Hz，4H，-CH2-OAr)，4.56(t，J＝6Hz，4H，-CH2-OCOR)，4.70(d，J＝6Hz，1H，桥H)，5.08(t，J＝6Hz，1H，桥H)，5.40(q，J＝6Hz，1H，环H)，5.46(m，1H，环H)，5.82(d，J＝10.7Hz，2H，烯H)，6.18(dd，J＝17Hz，J′＝10.7 Hz，2H，烯H)，6.48(d，J＝17Hz，2H，烯H)，6.95(d，J＝8.3Hz，2H，芳香H)，7.0(d，J＝8.3Hz，2H，芳香H)，7.95(d，J＝8.3Hz，2H，芳香H)，8.05(d，J＝8.3Hz，2H-芳香H).
实施例3
2，5-双[4’-(2-丙烯酰氧基乙氧基)联苯基-4-羰氧基]-1，4；3，6-二脱水-D-甘露糖醇
使用1，4；3，6-二脱水-D-甘露糖醇，按类似于实施例1中的方法制备该化合物。
产率：1.18g(约等于12％)，m.p.＞195℃。1H-NMR(200MHz，CDCl3)：δ＝3.82(dd，J＝6.3Hz，J′＝3Hz，2H，-CH2-，环H)，3.88(dd，J＝6.3Hz，J′＝3Hz，2H，-CH2-，环H)，4.15(t，J＝6Hz，4H，-CH2-OAr)，4.4(t，J＝6Hz，4H，-CH2-OCOR)，4.8(m，2H，桥H)，5.25(m，1H，桥H)，5.35(m，1H，环H)，5.85(d，J＝10.4Hz，2H，烯、H)，6.15(dd，J＝16Hz，J′＝10.4Hz，2H，烯H)，6.4(d，J＝16Hz，2H，烯、H)，7.1(d，J＝8.5Hz，4H，芳香H)，7.55(d，J＝8.5Hz，4H，芳香H)，8.0(d，J＝8.5Hz，4H，芳香H)，8.1(d，J＝8.5Hz，4H，芳香H).
实施例4
2，5-双[4’-(2-丙烯酰氧基乙氧基)联苯基-4-羰氧基]-1，4；3，6-二脱水-L-艾杜糖醇
使用1，4；3，6-二脱水-L-艾杜糖醇，按类似于实施例1中的方法制备该化合物。
产率：1.89g(约等于19％)，m.p.＞195℃。1H-NMR(200 MHz，CDCl3)：δ＝3.93(dd，J＝11.0Hz，J′＝3.0Hz，2H，-CH2-，环H)，3.98(dd，J＝11.0Hz，J′＝3Hz，2H，-CH2-，环H)，4.30(t，J＝6Hz，4H，-CH2-OAr)，4.50(t，J＝6Hz，4H，-CH2-OCOR)，5.35(s，2H，桥H)，5.65(dd，J＝11.0Hz，J′＝3Hz，2H，桥H)，5.90(d，J＝10.7Hz，2H，烯.H)，6.20(dd，J＝16.0Hz，J′＝10.7Hz，2H，烯H)，6.55(d，J＝16Hz，2H，烯H)，7.1(d，J＝8.7Hz，4H，芳香H)，7.50(d，J＝8.7Hz，4H，芳香H)，8.12(d，J＝8.7Hz，4H，芳香H)，8.13(d，J＝8.7Hz，4H，芳香H).
实施例5
2，5-双[4’-(2-丙烯酰氧基乙氧基)联苯基-4-羰氧基]-1，4；3，6-二脱水-L-艾杜糖醇
使用(R，R)-酒石酸二乙酯，按类似于实施例1中的方法制备该化合物。
产率：2.22g(约等于20％)，m.p.146℃。1H-NMR(200 MHz，CDCl3)：δ＝1.28(t，J＝6.9Hz，6H，酯CH3)，4.15(q，J＝6.9Hz，4H，酯CH2)，4.3(t，J＝6.0Hz，4H，-CH2-O-arom.)，4.55(t，J＝6.0Hz，4H，-CH2-O-COR)，5.88(d，J＝11.3Hz，2H，烯H)，6.04(s，2H，-CH(OR)(CO2R))，6.16(dd，J＝17.3，J′＝11.3Hz，2H，烯H)，6.48(d，J＝17.3Hz，1H，烯H)，7.05(d，J＝8.6Hz，4H，芳香H)，7.57(d，J＝8.6Hz，4H，芳香H)，7.68(d，J＝7.6Hz，4H，芳香H)，8.16(d，J＝7.6Hz，4H，芳香H).
在下表中给出的化合物(它们具有类似的物理性能)也能够通过与前面描述的方法类似的方法制备。
表1手性基团：
表2手性基团：
表3手性基团：
表4手性基团：
表5手性基团：
表6手性基团：
表7
该化合物能够由类似于实施例2的方法合成。
手性基团：实施例35 n＝4 HTP：41.5μm-1实施例36 n＝6 HTP：44.7μm-1实施例37 n＝8 HTP：47.7μm-1实施例38 n＝11 HTP：52.3μm-1
HTP＝螺旋扭转能
实施例39-42的化合物是由与实施例2的操作程序类似的操作程序，通过与甲基4，6-亚苄基-α-D-吡喃葡糖苷反应而获得的。
表8
手性基团：
实施例43-47的化合物是由类似于实施例2的方法，通过手性基团与4’-(ω-乙烯氧基)亚烷基氧基苯基-4-羧酸反应而获得的。
手性基团：
Claims (7)
1、可聚合的、手性的化合物，它含有至少一个二价或多价手性基团、至少一个可聚合基团、至少一个间隔基团和至少一个介晶基团。
2、根据权利要求1的化合物，它具有以下结构式
(Z-Y-A-Y-M-Y-)nX I，其中，在每一种情况下相互独立地，A 是间隔基，M 是介晶基，Y 是直接的键，O，S，COO，OCO，CON(R)或N(R)CO，Z 是可聚合基团，n 是2-6的数，X 是手性基团和R 是C1-C4烷基或氢。
3、根据权利要求2的化合物，其中介晶基团是具有以下结构式的基团
(T-Y1)r-T其中，每一个T独立地是亚环烷基，芳族基或杂芳族基，每一个Y1独立地是O，COO，OCO，CH2O，OCH2，CH＝N，N＝CH或直接的键，和r 是0-3。
4、根据权利要求3的化合物，其中r是0或1。
5、根据权利要求2的化合物，其中n是2。
6、根据权利要求2的化合物，其中X是 
其中L是C1-C4烷基，C1-C4烷氧基，卤素，COOR，OCOR，CONHR或NHCOR，这里R如上所定义。
7、根据权利要求1的化合物的用途，用于光电显示器或作为向列型或胆甾型液晶的手性掺杂剂、来生产能反射颜色的层。
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP4342280.2 | 1993-12-11 | ||
| DE4342280A DE4342280A1 (de) | 1993-12-11 | 1993-12-11 | Polymerisierbare chirale Verbindungen und deren Verwendung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1141645A true CN1141645A (zh) | 1997-01-29 |
| CN1075105C CN1075105C (zh) | 2001-11-21 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN94194817A Expired - Lifetime CN1075105C (zh) | 1993-12-11 | 1994-12-06 | 可聚合的手性化合物和它们的用途 |
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| Country | Link |
|---|---|
| US (2) | US5780629A (zh) |
| EP (1) | EP0739403B1 (zh) |
| JP (1) | JP4036891B2 (zh) |
| KR (1) | KR100342339B1 (zh) |
| CN (1) | CN1075105C (zh) |
| DE (2) | DE4342280A1 (zh) |
| WO (1) | WO1995016007A1 (zh) |
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| DE3333677A1 (de) * | 1983-09-17 | 1985-04-04 | Merck Patent Gmbh, 6100 Darmstadt | Fluessigkristall-phase |
| DE3604898A1 (de) * | 1986-02-17 | 1987-08-20 | Hoechst Ag | Chirale umsetzungsprodukte aus mesogenen molekuelbausteinen und bifunktionell reaktionsfaehigen weinsaeurederivaten und ihre verwendung als dotierstoff in fluessigkristall-phasen |
| US5011623A (en) * | 1988-07-20 | 1991-04-30 | Canon Kabushiki Kaisha | Nonlinear optical material and nonlinear optical device |
| DE3917196A1 (de) * | 1989-05-26 | 1990-12-13 | Basf Ag | Neue monomere und ihre verwendung zur herstellung eines wiederholt loeschbaren und beschreibbaren laseroptischen aufzeichnungselements |
| JPH03128371A (ja) * | 1989-07-12 | 1991-05-31 | Mitsubishi Rayon Co Ltd | 光学活性体及び液晶組成物 |
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1994
- 1994-12-06 DE DE59408401T patent/DE59408401D1/de not_active Expired - Lifetime
- 1994-12-06 KR KR1019960703045A patent/KR100342339B1/ko not_active IP Right Cessation
- 1994-12-06 CN CN94194817A patent/CN1075105C/zh not_active Expired - Lifetime
- 1994-12-06 WO PCT/EP1994/004055 patent/WO1995016007A1/de active IP Right Grant
- 1994-12-06 EP EP95903794A patent/EP0739403B1/de not_active Expired - Lifetime
- 1994-12-06 US US08/647,900 patent/US5780629A/en not_active Expired - Lifetime
- 1994-12-06 JP JP51467995A patent/JP4036891B2/ja not_active Expired - Lifetime
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103343014A (zh) * | 2013-06-21 | 2013-10-09 | 惠州市华阳光学技术有限公司 | 一种液晶组合物 |
| WO2014201997A1 (zh) * | 2013-06-21 | 2014-12-24 | 惠州市华阳光学技术有限公司 | 一种液晶组合物 |
| US9617476B2 (en) | 2013-06-21 | 2017-04-11 | Huizhou Foryou Optical Technology Co., Ltd. | Liquid crystal composition |
| CN106458833A (zh) * | 2014-06-30 | 2017-02-22 | 日本瑞翁株式会社 | 聚合性化合物的制造中间体、其制造方法、组合物及稳定化方法 |
| US10538477B2 (en) | 2014-06-30 | 2020-01-21 | Zeon Corporation | Production intermediate of polymerizable compound, production method for same, composition, and stabilization method |
| CN105001878A (zh) * | 2015-07-31 | 2015-10-28 | 江苏和成新材料有限公司 | 一种可聚合手性液晶组合物及其应用 |
| CN105001878B (zh) * | 2015-07-31 | 2017-08-29 | 江苏和成新材料有限公司 | 一种可聚合手性液晶组合物及其应用 |
| WO2017148025A1 (zh) * | 2016-03-04 | 2017-09-08 | 京东方科技集团股份有限公司 | 胆甾相液晶组合物、液晶显示面板及其制备方法 |
| US10093858B2 (en) | 2016-03-04 | 2018-10-09 | Boe Technology Group Co., Ltd. | Cholesteric liquid crystal composition, liquid crystal display panel and preparation method thereof |
| CN113501758A (zh) * | 2021-09-10 | 2021-10-15 | 南京迈诺威医药科技有限公司 | 一种联苯化合物的制备方法 |
| CN113501758B (zh) * | 2021-09-10 | 2021-11-23 | 南京迈诺威医药科技有限公司 | 一种联苯化合物的制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| US5886242A (en) | 1999-03-23 |
| EP0739403A1 (de) | 1996-10-30 |
| EP0739403B1 (de) | 1999-06-09 |
| WO1995016007A1 (de) | 1995-06-15 |
| JPH09506088A (ja) | 1997-06-17 |
| KR100342339B1 (ko) | 2002-12-05 |
| DE4342280A1 (de) | 1995-06-14 |
| US5780629A (en) | 1998-07-14 |
| JP4036891B2 (ja) | 2008-01-23 |
| KR960706543A (ko) | 1996-12-09 |
| DE59408401D1 (de) | 1999-07-15 |
| CN1075105C (zh) | 2001-11-21 |
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