TWI798465B - Liquid crystal compound, liquid crystal composition, liquid crystal display element and liquid crystal display - Google Patents
Liquid crystal compound, liquid crystal composition, liquid crystal display element and liquid crystal display Download PDFInfo
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- TWI798465B TWI798465B TW108124577A TW108124577A TWI798465B TW I798465 B TWI798465 B TW I798465B TW 108124577 A TW108124577 A TW 108124577A TW 108124577 A TW108124577 A TW 108124577A TW I798465 B TWI798465 B TW I798465B
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- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 206
- 150000001875 compounds Chemical class 0.000 title claims abstract description 157
- 239000000203 mixture Substances 0.000 title claims abstract description 96
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 96
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 45
- 125000004980 cyclopropylene group Chemical group 0.000 claims abstract description 23
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims abstract description 18
- 125000004979 cyclopentylene group Chemical group 0.000 claims abstract description 17
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract description 13
- 125000003342 alkenyl group Chemical group 0.000 claims description 25
- 125000001153 fluoro group Chemical group F* 0.000 claims description 23
- 125000003545 alkoxy group Chemical group 0.000 claims description 22
- 229910052731 fluorine Inorganic materials 0.000 claims description 21
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 19
- 239000011737 fluorine Substances 0.000 claims description 12
- 125000004976 cyclobutylene group Chemical group 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000011159 matrix material Substances 0.000 claims description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 238000006467 substitution reaction Methods 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000005725 cyclohexenylene group Chemical group 0.000 claims description 2
- 125000004956 cyclohexylene group Chemical group 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims 1
- 230000037429 base substitution Effects 0.000 claims 1
- 235000019256 formaldehyde Nutrition 0.000 claims 1
- 230000000875 corresponding effect Effects 0.000 description 20
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- 238000002834 transmittance Methods 0.000 description 16
- 239000002994 raw material Substances 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 238000003756 stirring Methods 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 10
- 239000007788 liquid Substances 0.000 description 9
- 239000003208 petroleum Substances 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 8
- 239000000178 monomer Substances 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 230000036632 reaction speed Effects 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 125000004430 oxygen atom Chemical group O* 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 229910001220 stainless steel Inorganic materials 0.000 description 6
- 239000010935 stainless steel Substances 0.000 description 6
- 230000003287 optical effect Effects 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- -1 cyclopentylidene group Chemical group 0.000 description 4
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 4
- 238000005265 energy consumption Methods 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- ISQVBYGGNVVVHB-UHFFFAOYSA-N cyclopentylmethanol Chemical compound OCC1CCCC1 ISQVBYGGNVVVHB-UHFFFAOYSA-N 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 3
- 229910021641 deionized water Inorganic materials 0.000 description 3
- 125000005647 linker group Chemical group 0.000 description 3
- OEPBVXQEVBURGC-UHFFFAOYSA-N 4-bromo-2-fluoro-1-(trifluoromethyl)benzene Chemical compound FC1=CC(Br)=CC=C1C(F)(F)F OEPBVXQEVBURGC-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 230000001788 irregular Effects 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- LKOXSLOIMSYWPK-UHFFFAOYSA-N (3-propylcyclopentyl)methanol Chemical compound CCCC1CCC(CO)C1 LKOXSLOIMSYWPK-UHFFFAOYSA-N 0.000 description 1
- RPEPGIOVXBBUMJ-UHFFFAOYSA-N 2,3-difluorophenol Chemical compound OC1=CC=CC(F)=C1F RPEPGIOVXBBUMJ-UHFFFAOYSA-N 0.000 description 1
- SBSFDYRKNUCGBZ-UHFFFAOYSA-N 4-bromo-2-fluoro-1-(trifluoromethoxy)benzene Chemical compound FC1=CC(Br)=CC=C1OC(F)(F)F SBSFDYRKNUCGBZ-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-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
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- GUDMZGLFZNLYEY-UHFFFAOYSA-N cyclopropylmethanol Chemical compound OCC1CC1 GUDMZGLFZNLYEY-UHFFFAOYSA-N 0.000 description 1
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 1
- FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- OVEHNNQXLPJPPL-UHFFFAOYSA-N lithium;n-propan-2-ylpropan-2-amine Chemical compound [Li].CC(C)NC(C)C OVEHNNQXLPJPPL-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000013076 target substance Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- 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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/42—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40
- C09K19/44—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40 containing compounds with benzene rings directly linked
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/42—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40
- C09K19/46—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40 containing esters
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- 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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- Chemical & Material Sciences (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Liquid Crystal Substances (AREA)
Abstract
本發明涉及液晶化合物、液晶組合物、液晶顯示元件及液晶顯示器。本發明的液晶化合物為下述的式I所示的液晶化合物，
式I中，R表示環丙基、環戊基或者碳原子數為2-10的烷基中一個以上的-CH2-被亞環丙基或亞環戊基取代後得到的基團；Y表示-OCF3、-CF3、-CF2H或-OCF2H；Z表示單鍵、-CH2O-、-CF2O-或-COO-；
Description
本發明屬於液晶化合物領域。更具體地，涉及液晶化合物、液晶組合物、液晶顯示元件及液晶顯示器。 The invention belongs to the field of liquid crystal compounds. More specifically, it relates to a liquid crystal compound, a liquid crystal composition, a liquid crystal display element, and a liquid crystal display.
TFT-LCD面板的透過率是指背光源透過TFT-LCD面板前後的光強度之比。TFT-LCD是透過率只有3%~10%的低效率元件，當背光源的亮度為100時，從背光源入射的光通過面板的各層後，大部分被吸收，最終透過面板後的光亮度只有5，也就是說透過率只有5%，只有一少部分光可以有效的利用、被人眼捕獲。如果可以對液晶組合物的透過率進行提高，那麼就可以有效增加TFT-LCD面板的透過率，使得更多的光有效被利用；另一方面，也可以降低背光強度，從而實現節省能耗的目的，延長設備的使用時間。 The transmittance of the TFT-LCD panel refers to the ratio of light intensity before and after the backlight passes through the TFT-LCD panel. TFT-LCD is a low-efficiency element with a transmittance of only 3%~10%. When the brightness of the backlight is 100, most of the light incident from the backlight is absorbed after passing through the layers of the panel, and finally passes through the panel. Only 5, that is to say, the transmittance is only 5%, and only a small part of light can be effectively used and captured by human eyes. If the transmittance of the liquid crystal composition can be improved, then the transmittance of the TFT-LCD panel can be effectively increased, so that more light can be effectively used; on the other hand, the intensity of the backlight can also be reduced, thereby realizing energy saving. The purpose is to prolong the use time of the equipment.
另外，為了應對動態畫面顯示應用中存在的顯示畫面殘影和拖尾的問題，要求液晶顯示裝置具有快的反應速度，因此要求液晶組合物具有低的旋轉黏度γ1。另外，液晶組合物加電後的反應速度與液晶組合物的黏度，尤其是旋轉黏度γ1直接相關。 In addition, in order to deal with the problems of image sticking and smearing of the display screen in the application of dynamic screen display, the liquid crystal display device is required to have a fast response speed, so the liquid crystal composition is required to have a low rotational viscosity γ1. In addition, the reaction speed of the liquid crystal composition after being charged is directly related to the viscosity of the liquid crystal composition, especially the rotational viscosity γ1.
為了獲得透過率提高、旋轉黏度降低的用於液晶顯示的液晶化合物、液晶組合物，本申請的發明人等進行了深入研究後發現，藉由本發明的液晶化合物、液晶組合物能夠實現該目的，從而完成了本發明。 In order to obtain liquid crystal compounds and liquid crystal compositions for liquid crystal displays with improved transmittance and reduced rotational viscosity, the inventors of the present application have conducted in-depth research and found that the object can be achieved by the liquid crystal compound and liquid crystal composition of the present invention, The present invention has thus been accomplished.
本發明的一個目的在於提供一種液晶化合物。 One object of the present invention is to provide a liquid crystal compound.
本發明的另一目的在於提供一種含有前述液晶化合物的液晶組合物。 Another object of the present invention is to provide a liquid crystal composition containing the aforementioned liquid crystal compound.
本發明的又一目的在於提供又一種液晶組合物。 Another object of the present invention is to provide another liquid crystal composition.
本發明的再一目的在於提供一種包含前述液晶組合物的液晶顯示元件或液晶顯示器。 Another object of the present invention is to provide a liquid crystal display element or a liquid crystal display comprising the aforementioned liquid crystal composition.
做為本發明的一個方案的液晶化合物，其為下述的式I所示的液晶化合物：
其中：R表示環丙基、環戊基或者碳原子數為2-10的烷基中一個以上的-CH2-被亞環丙基或亞環戊基取代後得到的基團；Y表示-OCF3、-CF3、-CF2H或-OCF2H；Z表示單鍵、-CH2O-、-CF2O-或-COO-；
做為本發明的一個方案的液晶組合物，其含有做為上述本發明的一個方案的液晶化合物。 The liquid crystal composition which is one aspect of the present invention contains the liquid crystal compound which is one aspect of the present invention described above.
做為本發明的又一方案的液晶組合物，其包含一種或多種式II所示化合物、一種或多種式III所示化合物以及一種或多種式IV所示化合物，
其中，式II中，R’表示環丙基、環戊基或者碳原子數為2-10的烷基中一個以上的-CH2-被亞環丙基或亞環戊基取代後得到的基團；Y’表示-F、-OCF3、-CF3、-CF2H或-OCF2H；Z1表示單鍵、-CH2O-、-CF2O-或-COO-；
做為本發明的另一方案的液晶顯示元件或液晶顯示器，其包含前述的液晶組合物，該液晶顯示元件或液晶顯示器為主動矩陣顯示元件或顯示器或者被動矩陣顯示元件或顯示器。 As another aspect of the present invention, a liquid crystal display element or a liquid crystal display comprises the aforementioned liquid crystal composition, and the liquid crystal display element or liquid crystal display is an active matrix display element or display or a passive matrix display element or display.
前述的式I所示化合物、式II所示化合物具有垂直介電常數大、旋轉黏度低、溶解度高的特點。另外，式I所示化合物、式II所示化合物具有旋轉 黏度低、與其他化合物互溶性好的特點。較低的旋轉黏度更有利於提高液晶組合物的反應速度。藉由在液晶組合物中採用式I、式II所示的液晶化合物，能夠利用該液晶化合物的大的垂直介電常數從而有利於提高液晶組合物的透過率，從而能夠提高液晶顯示元件或液晶顯示器的透過率，使更多的背光穿透液晶顯示元件或液晶顯示器，提高背光利用率，從而提高其亮度，降低能源消耗，達到節能降耗的目的。 The aforementioned compounds represented by formula I and formula II have the characteristics of large vertical dielectric constant, low rotational viscosity and high solubility. In addition, the compound shown in formula I and the compound shown in formula II have rotation Low viscosity, good miscibility with other compounds. A lower rotational viscosity is more conducive to increasing the reaction speed of the liquid crystal composition. By using the liquid crystal compound shown in formula I and formula II in the liquid crystal composition, the large vertical dielectric constant of the liquid crystal compound can be used to help improve the transmittance of the liquid crystal composition, thereby improving the performance of the liquid crystal display element or liquid crystal. The transmittance of the display allows more backlight to penetrate the liquid crystal display element or liquid crystal display, improving the utilization rate of the backlight, thereby increasing its brightness, reducing energy consumption, and achieving the purpose of saving energy and reducing consumption.
做為本發明的一個方案的液晶化合物為下述的式I所示的液晶化合物：
式I所示的液晶化合物具有二苯並呋喃結構，該結構包含的兩個氟原子和一個氧原子為液晶化合物提供較大的垂直介電常數。由於二苯並呋喃結構包含的氟原子與液晶化合物長軸方向存在夾角，從而使得氟原子形成的介電各向異性能夠分解為平行和垂直於液晶化合物長軸方向的平行介電常數和垂直介電常數。由於兩個氟原子產生的平行介電常數方向相反、大小相等，從而氟原子未提高液晶化合物的平行介電常數，只提高了液晶化合物的垂直介電常數。並且，氧原子只在垂直於液晶化合物長軸方向存在介電各向異性分量。Y基團做為端基為液晶化合物提供較大的平行介電常數，其絕對值大小與氟原子和氧原子提供的垂直介電常數相近。R基團降低了液晶化合物的對稱性，形成不規則的結構，阻礙液晶化合物形成有規則的晶體結構，有助於液晶化合物保持液晶態，並有效提高液晶化合物的清亮點。從而，式I所示的化合物的介電各向異性的絕對值較小，接近中性，但具有垂直介電常數大、旋轉黏度低、溶解度高的特點。藉由在液晶組合物中採用前述的液晶化合物，能夠利用該液晶化合物的大的垂直介電常數從而有利於提高液晶組合物的透過率，從而能夠提高液晶顯示元件或液晶顯示器的透過率，使更多的背光穿透液晶顯示元件或液晶顯示器，提高背光利用率，從而提高其亮度，降低能源消耗，達到節能降耗的目的。 另外，式I所示化合物具有旋轉黏度低、與其他化合物互溶性好的特點。較低的旋轉黏度更有利於提高液晶組合物的反應速度。 The liquid crystal compound represented by formula I has a dibenzofuran structure, and the structure contains two fluorine atoms and one oxygen atom to provide the liquid crystal compound with a large vertical dielectric constant. Due to the included angle between the fluorine atoms contained in the dibenzofuran structure and the long axis direction of the liquid crystal compound, the dielectric anisotropy formed by the fluorine atoms can be decomposed into the parallel dielectric constant and the perpendicular dielectric constant parallel to and perpendicular to the long axis direction of the liquid crystal compound. electric constant. Since the parallel dielectric constants produced by the two fluorine atoms are opposite in direction and equal in size, the fluorine atoms do not increase the parallel dielectric constant of the liquid crystal compound, but only increase the vertical dielectric constant of the liquid crystal compound. Also, oxygen atoms have a dielectric anisotropy component only in the direction perpendicular to the long axis of the liquid crystal compound. The Y group serves as an end group to provide a large parallel dielectric constant for the liquid crystal compound, and its absolute value is similar to the vertical dielectric constant provided by the fluorine atom and the oxygen atom. The R group reduces the symmetry of the liquid crystal compound, forms an irregular structure, prevents the liquid crystal compound from forming a regular crystal structure, helps the liquid crystal compound to maintain a liquid crystal state, and effectively improves the clearing point of the liquid crystal compound. Therefore, the absolute value of the dielectric anisotropy of the compound represented by formula I is small and close to neutral, but it has the characteristics of large vertical dielectric constant, low rotational viscosity and high solubility. By using the aforementioned liquid crystal compound in the liquid crystal composition, the large vertical dielectric constant of the liquid crystal compound can be used to help improve the transmittance of the liquid crystal composition, thereby improving the transmittance of the liquid crystal display element or liquid crystal display, making More backlight penetrates the liquid crystal display element or liquid crystal display to increase the utilization rate of the backlight, thereby increasing its brightness, reducing energy consumption, and achieving the purpose of saving energy and reducing consumption. In addition, the compound represented by formula I has the characteristics of low rotational viscosity and good miscibility with other compounds. A lower rotational viscosity is more conducive to increasing the reaction speed of the liquid crystal composition.
做為前述的式I所示的液晶組合物中R表示環丙基、環戊基或碳原子數為2-10的烷基中的一個以上的-CH2-被亞環丙基或亞環戊基取代後得到的基團。碳原子數為2-10的烷基中的一個以上的-CH2-被亞環丙基或亞環戊基取代後得到的基團可以列舉出甲基亞環丙基、乙基亞環丙基、丙基亞環丙基、異丙基亞環丙基、正丁基亞環丙基、異丁基亞環丙基、叔丁基亞環丙基、甲基亞環戊基、乙基亞環戊基、丙基亞環戊基、異丙基亞環戊基、正丁基亞環戊基、異丁基亞環戊基等。R所示的基團中，從液晶化合物旋轉黏度、溶解度和清亮點考慮，較佳的是環丙基或環戊基。Z表示的連接基團中，較佳為-CH2O-，-CH2O-相對於單鍵、-CF2O-或-COO-能夠為液晶化合物提供更大的垂直介電常數。 In the liquid crystal composition shown in the aforementioned formula I, R represents one or more of cyclopropyl, cyclopentyl, or an alkyl group with 2-10 carbon atoms -CH 2 -by cyclopropylene or cyclopropylene The group obtained after pentyl substitution. The groups obtained by substituting one or more -CH 2 - in the alkyl group having 2 to 10 carbon atoms by cyclopropylene or cyclopentylene include methylcyclopropylene, ethylcyclopropylene radical, propylcyclopropylene, isopropylcyclopropylene, n-butylcyclopropylene, isobutylcyclopropylene, tert-butylcyclopropylene, methylcyclopentylene, ethyl Cyclopentylene, propylcyclopentylene, isopropylcyclopentylene, n-butylcyclopentylene, isobutylcyclopentylene and the like. Among the groups represented by R, a cyclopropyl group or a cyclopentyl group is preferable in view of the rotational viscosity, solubility and clearing point of the liquid crystal compound. Among the linking groups represented by Z, -CH 2 O- is preferred. Compared with single bonds, -CF 2 O- or -COO-, -CH 2 O- can provide liquid crystal compounds with a larger vertical dielectric constant.
可選的，前述式I所示液晶化合物選自式I1-I32所示化合物組成的群組，
其中：R表示環丙基、環戊基或者碳原子數為2-10的烷基中一個以上的-CH2-被亞環丙基或亞環戊基取代後得到的基團；
在本發明的一個實施方式中，上述式I所示化合物中，從液晶化合物旋轉黏度、溶解度和清亮點考慮，較佳地，式I所示化合物選自下述的化學式所示的化合物組成的群組，
前述的式I所示的化合物可以藉由後述記載的實施例所示的方法以及在這些方法中使用與目標物質匹配的已知的代替反應和原料來進行製造。 The compound represented by the aforementioned formula I can be produced by the methods shown in the examples described later and using known substitution reactions and raw materials matching the target substance in these methods.
做為本發明的一個方案的液晶組合物含有前述的式I所示的液晶化合物。液晶組合物中，除了式I所示的化合物之外，還可以含有式I所示的液晶化合物之外的液晶化合物以及其他添加材料。藉由在液晶組合物中含有式I所示的液晶化合物，能夠利用該液晶化合物的大的垂直介電常數從而有利於提高液晶組合物的透過率，使更多的背光穿透液晶顯示元件或液晶顯示器，提高背光利用率。並且，式I所示化合物具有旋轉黏度低、與其他化合物互溶性好的特點。較低的旋轉黏度更有利於提高液晶組合物的反應速度。 The liquid crystal composition as one aspect of the present invention contains the liquid crystal compound represented by the aforementioned formula I. In addition to the compound represented by the formula I, the liquid crystal composition may contain liquid crystal compounds other than the liquid crystal compound represented by the formula I and other additive materials. By including the liquid crystal compound shown in formula I in the liquid crystal composition, the large vertical dielectric constant of the liquid crystal compound can be used to help improve the transmittance of the liquid crystal composition, so that more backlight can penetrate the liquid crystal display element or LCD display, improve backlight utilization. Moreover, the compound represented by formula I has the characteristics of low rotational viscosity and good miscibility with other compounds. A lower rotational viscosity is more conducive to increasing the reaction speed of the liquid crystal composition.
做為本發明的又一個方案的液晶組合物，其包含一種或多種式II所示化合物、一種或多種式III所示化合物以及一種或多種式IV所示化合物，
其中，式II中，R’表示環丙基、環戊基或者碳原子數為2-10的烷基中一個以上的-CH2-被亞環丙基或亞環戊基取代後得到的基團；Y’表示-F、-OCF3、-CF3、-CF2H或-OCF2H；Z1表示-CH2O-、-CF2O-或-COO-；
前述的本發明的又一方案的液晶組合物中，式II所示的液晶化合物具有二苯並呋喃結構，該結構包含的兩個氟原子和一個氧原子為液晶化合物提供較大的垂直介電常數。由於二苯並呋喃結構包含的氟原子與液晶化合物長軸方向存在夾角，從而使得氟原子形成的介電各向異性能夠分解為平行和垂直於液晶化合物長軸方向的平行介電常數和垂直介電常數。由於兩個氟原子產生的平行介電常數方向相反、大小相等，從而氟原子未提高液晶化合物的平行介電常數，只提高了液晶化合物的垂直介電常數。並且，氧原子只在垂直於液晶化合物長軸方向存在介電各向異性分量。Y’基團做為端基為液晶化合物提供較大的平行介電常數，其絕對值大小與氟原子和氧原子提供的垂直介電常數相近。R’基團降低了液晶化合物的對稱性，形成不規則的結構，阻礙液晶化合物形成有規則的晶體結構，有助於液晶化合物保持液晶態，並有效提高液晶化合物的清亮點。因此，式II所示的液晶化合物的介電各向異性的絕對值較小，接近中性，但具有垂直介電常數大、旋轉黏度低、溶解度高的特點。藉由在液晶組合物中採用前述的式II所示的液晶化合物，能夠利用該液晶化合物的大的垂直介電常數從而有利於提高液晶組合物的透過率，從而能夠提高液晶顯示元件或液 晶顯示器的透過率，使更多的背光穿透液晶顯示元件或液晶顯示器，提高背光利用率，從而提高其亮度，降低能源消耗，達到節能降耗的目的。並且，前述的式II所示化合物具有旋轉黏度低、與其他化合物互溶性好的特點。較低的旋轉黏度更有利於提高液晶組合物的反應速度。 In the aforementioned liquid crystal composition of another solution of the present invention, the liquid crystal compound shown in formula II has a dibenzofuran structure, and the two fluorine atoms and one oxygen atom contained in the structure provide a larger vertical dielectric for the liquid crystal compound. constant. Due to the included angle between the fluorine atoms contained in the dibenzofuran structure and the long axis direction of the liquid crystal compound, the dielectric anisotropy formed by the fluorine atoms can be decomposed into the parallel dielectric constant and the perpendicular dielectric constant parallel to and perpendicular to the long axis direction of the liquid crystal compound. electrical constant. Since the parallel dielectric constants produced by the two fluorine atoms are opposite in direction and equal in size, the fluorine atoms do not increase the parallel dielectric constant of the liquid crystal compound, but only increase the vertical dielectric constant of the liquid crystal compound. Also, oxygen atoms have a dielectric anisotropy component only in the direction perpendicular to the long axis of the liquid crystal compound. The Y' group is used as an end group to provide a large parallel dielectric constant for liquid crystal compounds, and its absolute value is similar to the vertical dielectric constant provided by fluorine atoms and oxygen atoms. The R' group reduces the symmetry of the liquid crystal compound, forms an irregular structure, prevents the liquid crystal compound from forming a regular crystal structure, helps the liquid crystal compound to maintain a liquid crystal state, and effectively improves the clearing point of the liquid crystal compound. Therefore, the absolute value of the dielectric anisotropy of the liquid crystal compound represented by formula II is small and close to neutral, but it has the characteristics of large vertical dielectric constant, low rotational viscosity and high solubility. By using the liquid crystal compound shown in the aforementioned formula II in the liquid crystal composition, the large vertical dielectric constant of the liquid crystal compound can be used to help improve the transmittance of the liquid crystal composition, thereby improving the performance of the liquid crystal display element or liquid crystal. The transmittance of the crystal display allows more backlight to penetrate the liquid crystal display element or liquid crystal display, and improves the utilization rate of the backlight, thereby increasing its brightness, reducing energy consumption, and achieving the purpose of saving energy and reducing consumption. Moreover, the aforementioned compound represented by formula II has the characteristics of low rotational viscosity and good miscibility with other compounds. A lower rotational viscosity is more conducive to increasing the reaction speed of the liquid crystal composition.
式III所示化合物為正介電各向異性，藉由式III所示化合物來調節液晶組合物的驅動電壓。 The compound represented by formula III has positive dielectric anisotropy, and the driving voltage of the liquid crystal composition can be adjusted by the compound represented by formula III.
前述式II所示化合物占液晶組合物總質量百分比含量為1-15%，較佳為2-10%；式III所示化合物占液晶組合物總質量百分比含量為1-60%，較佳為10-50%；式IV所示化合物占液晶組合物總質量百分比含量為10-70%，較佳為20-60%。 The compound represented by formula II accounts for 1-15% of the total mass percentage of the liquid crystal composition, preferably 2-10%; the compound represented by formula III accounts for 1-60% of the total mass percentage of the liquid crystal composition, preferably 10-50%; the compound represented by formula IV accounts for 10-70% of the total mass percentage of the liquid crystal composition, preferably 20-60%.
做為前述的式II所示的液晶組合物中R’表示環丙基、環戊基或碳原子數為2-10的烷基中的一個以上的-CH2-被亞環丙基或亞環戊基取代後得到的基團。碳原子數為2-10的烷基中的一個以上的-CH2-被亞環丙基或亞環戊基取代後得到的基團可以列舉出甲基亞環丙基、乙基亞環丙基、丙基亞環丙基、異丙基亞環丙基、正丁基亞環丙基、異丁基亞環丙基、叔丁基亞環丙基、甲基亞環戊基、乙基亞環戊基、丙基亞環戊基、異丙基亞環戊基、正丁基亞環戊基、異丁基亞環戊基。R’所示的基團中，從液晶化合物旋轉黏度、溶解度和清亮點考慮較佳的是環丙基或環戊基。Z1表示的連接基團中，較佳為-CH2O-，-CH2O-相對於單鍵、-CF2O-或-COO-能夠為液晶化合物提供更大的垂直介電常數。 In the liquid crystal composition shown in the aforementioned formula II, R' represents one or more of -CH 2 - from cyclopropylidene or alkylene in cyclopropyl, cyclopentyl, or an alkyl group with 2-10 carbon atoms. The group obtained after cyclopentyl substitution. The groups obtained by substituting one or more -CH 2 - in the alkyl group having 2 to 10 carbon atoms by cyclopropylene or cyclopentylene include methylcyclopropylene, ethylcyclopropylene radical, propylcyclopropylene, isopropylcyclopropylene, n-butylcyclopropylene, isobutylcyclopropylene, tert-butylcyclopropylene, methylcyclopentylene, ethyl Cyclopentylene, propylcyclopentylene, isopropylcyclopentylene, n-butylcyclopentylene, isobutylcyclopentylene. Among the groups represented by R', a cyclopropyl group or a cyclopentyl group is preferable in view of the rotational viscosity, solubility, and clearing point of the liquid crystal compound. Among the linking groups represented by Z 1 , -CH 2 O- is preferred. Compared with single bonds, -CF 2 O- or -COO-, -CH 2 O- can provide liquid crystal compounds with a larger vertical dielectric constant.
做為前述的式II所示的液晶化合物中Y1所表示的基團，從提高平行介電常數從而使液晶化合物的介電各向異性絕對值接近零、從提高液晶化合物的清亮點方面考慮，較佳為-CF3、-OCF3、-OCF2H或-OCH2F。 As the group represented by Y in the liquid crystal compound shown in the aforementioned formula II, from the perspective of improving the parallel dielectric constant so that the absolute value of the dielectric anisotropy of the liquid crystal compound is close to zero, and from the perspective of improving the clearing point of the liquid crystal compound , preferably -CF 3 , -OCF 3 , -OCF 2 H or -OCH 2 F.
可選的，前述一種或多種式II所示化合物選自式II1-II40所示化合物組成的群組，前述一種或多種式III所示化合物選自式III1-III27所示化合物組成的群組，前述一種或多種式IV所示化合物選自式IV1-IV16所示化合物組成的群組。 Optionally, the aforementioned one or more compounds represented by formula II are selected from the group consisting of compounds represented by formula II1-II40, and the aforementioned one or more compounds represented by formula III are selected from the group consisting of compounds represented by formula III1-III27, The aforementioned one or more compounds represented by formula IV are selected from the group consisting of compounds represented by formula IV1-IV16.
其中，式II1-II40中的R’與前述的式II所示化合物中的R’的含義相同，各自獨立地表示環丙基、環戊基或者碳原子數為2-10的烷基中一個以上的-CH2-被亞環丙基或亞環戊基取代後得到的基團；式II16-II30、II36-II40中的
較佳地，上述一種或多種式II所示化合物選自下述的化學式所示化合物組成的群組，
做為本發明的又一個方案的液晶組合物，在一個實施方式中，可選的，還可以包含一種或多種式V所示化合物：
其中：R4、R5各自獨立地表示碳原子數為1-10的烷基、碳原子數為1-10的烷氧基、碳原子數為2-10的直鏈烯基或碳原子數為3-8的直鏈烯氧基；
可選的，前述一種或多種式V所示化合物選自式V1-V10所示化合物組成的群組，
其中，R41表示碳原子數為2-6的烷基，R42表示碳原子數為2-6的烯基、R51表示碳原子數為1-6的烷基，R52表示碳原子數為1-6的烷氧基；R43、R53各自獨立地表示碳原子數為1-6的烷基。 Among them, R 41 represents an alkyl group with 2-6 carbon atoms, R 42 represents an alkenyl group with 2-6 carbon atoms, R 51 represents an alkyl group with 1-6 carbon atoms, and R 52 represents an alkyl group with 1-6 carbon atoms. is an alkoxy group of 1-6; R 43 and R 53 each independently represent an alkyl group with 1-6 carbon atoms.
上述式V1-V6所示的化合物具有較高的清亮點和彈性常數，尤其是展曲彈性常數K33，有利於提升液晶組合物的信賴性及反應速度。 The compounds represented by the above formulas V1-V6 have relatively high clearing points and elastic constants, especially the splay elastic constant K 33 , which is beneficial to improve the reliability and response speed of the liquid crystal composition.
在含有上述的式V1-V6所示化合物組成的群組中的化合物的情況下，式V1-V6所示化合物的總量占液晶組合物總質量百分比含量為1-40%，較佳為5-25%。 In the case of the compounds in the group consisting of the compounds represented by the above formulas V1-V6, the total amount of the compounds represented by the formulas V1-V6 accounts for 1-40% of the total mass percentage of the liquid crystal composition, preferably 5% -25%.
上述式V7-V10所示的化合物相對於式V1-V6所示的化合物具有更高的清亮點，一般高於200℃，可以更加顯著地提升液晶組合物清亮點。 The compounds represented by the above formulas V7-V10 have a higher clearing point than the compounds represented by the formulas V1-V6, generally higher than 200° C., which can significantly increase the clearing point of the liquid crystal composition.
在含有上述的式V7-V10所示化合物組成的群組中的化合物的情況下，上述式V7-V10所示化合物的總量占液晶組合物總質量百分比含量為1-20%，較佳為5-15%。 In the case of compounds in the group consisting of compounds represented by the above formulas V7-V10, the total amount of the compounds represented by the above formulas V7-V10 accounts for 1-20% of the total mass percentage of the liquid crystal composition, preferably 5-15%.
做為本發明的又一個方案的液晶組合物，在一個實施方式中，可選的，還可以包含一種或多種式VI所示化合物：
其中，R6、R7各自獨立地表示碳原子數為1-10的烷基、氟取代的碳原子數為1-10的烷基、碳原子數為1-10的烷氧基、氟取代的碳原子數為1-10的烷氧基、碳原子數為2-10的直鏈烯基、氟取代的碳原子數為2-10的直鏈烯基、碳原子數為3-8的直鏈烯氧基或氟取代的碳原子數為3-8的直鏈烯氧基，所述R6、R7所示基團中任意一個或多個不相連的-CH2-任選各自獨立地被亞環戊基、亞環丁基或亞環丙基取代；
上述式VI所示化合物具有較大的垂直介電，可以根據不同使用條件調節液晶組合物的垂直介電常數，液晶組合物可以保持低旋轉黏度，以在稍微犧牲反應速度的前提下進一步提升液晶組合物的垂直介電常數，從而獲得在維持一定的反應速度的基礎上透過率提高了的液晶組合物。 The compound shown in the above formula VI has a large vertical dielectric constant, and the vertical dielectric constant of the liquid crystal composition can be adjusted according to different use conditions. The liquid crystal composition can maintain a low rotational viscosity, so as to further improve the liquid crystal under the premise of slightly sacrificing the reaction speed. The vertical permittivity of the composition is adjusted to obtain a liquid crystal composition with increased transmittance while maintaining a certain reaction speed.
在含有上述的式VI所示化合物組成的群組中的化合物的情況下，上述一種或多種式VI所示化合物占液晶組合物總質量百分比含量為1-30%，較佳為10-25%。 In the case of compounds in the group consisting of compounds represented by the above formula VI, the content of one or more compounds represented by the above formula VI in the total mass percentage of the liquid crystal composition is 1-30%, preferably 10-25% .
可選的，前述一種或多種式VI所示化合物選自式VI1-VI21所示化合物組成的群組，
其中，R6、R7各自獨立地表示碳原子數為1-10的烷基、碳原子數為1-10的烷氧基、碳原子數為2-10的直鏈烯基或碳原子數為3-8的直鏈烯氧基，所述R6、R7所示基團中任意一個或多個不相連的-CH2-任選各自獨立地被亞環戊基、亞環丁基或亞環丙基取代。 Wherein, R 6 and R 7 each independently represent an alkyl group with 1-10 carbon atoms, an alkoxy group with 1-10 carbon atoms, a straight-chain alkenyl group with 2-10 carbon atoms, or an alkyl group with 1-10 carbon atoms. 3-8 linear alkenyloxy groups, any one or more unconnected -CH 2 - in the groups represented by R 6 and R 7 are optionally independently replaced by cyclopentylene, cyclobutylene Or cyclopropylene substitution.
做為本發明的又一個方案的液晶組合物，在一個實施方式中，可選的，還可以包含一種或多種式VII所示化合物：
其中，R8、R9各自獨立地表示碳原子數為1-10的烷基、氟取代的碳原子數為1-10的烷基、碳原子數為1-10的烷氧基、氟取代的碳原子數為1-10的烷氧基、碳原子數為2-10的直鏈烯基、氟取代的碳原子數為2-10的直鏈烯基、碳原子數為3-8的直鏈烯氧基或氟取代的碳原子數為3-8的直鏈烯氧基，並且R8、R9所示基團中任意一個或多個-CH2-任選各自獨立地被亞環戊基、亞環丁基或亞環丙基取代；X表示O、S或CH2O。 Wherein, R 8 and R 9 each independently represent an alkyl group with 1-10 carbon atoms, an alkyl group with 1-10 carbon atoms substituted by fluorine, an alkoxy group with 1-10 carbon atoms, or an alkyl group with 1-10 carbon atoms substituted by fluorine. Alkoxy groups with 1-10 carbon atoms, straight-chain alkenyl groups with 2-10 carbon atoms, straight-chain alkenyl groups with 2-10 carbon atoms substituted by fluorine, and straight-chain alkenyl groups with 3-8 carbon atoms A linear alkenyloxy group or a straight chain alkenyloxy group with 3-8 carbon atoms substituted by fluorine, and any one or more -CH 2 - in the groups represented by R 8 and R 9 are optionally independently subdivided Substituted by cyclopentyl, cyclobutylene or cyclopropylene; X represents O, S or CH 2 O.
上述式VII所示的化合物相對於式VI所示化合物具有更大的垂直介電，可以藉由少量添加式VII所示的化合物獲得更大的垂直介電，有利於進一步提高液晶組合物的透過率。 The compound shown in the above formula VII has a larger vertical dielectric relative to the compound shown in the formula VI, and a larger vertical dielectric can be obtained by adding a small amount of the compound shown in the formula VII, which is conducive to further improving the permeability of the liquid crystal composition. Rate.
在含有上述式VII所示的化合物的情況下，上述一種或多種式VII所示化合物占液晶組合物總質量百分比含量為1-15%，較佳為2-10%。 In the case of containing the compound represented by the above formula VII, the content of one or more compounds represented by the above formula VII in the total mass percentage of the liquid crystal composition is 1-15%, preferably 2-10%.
可選的，前述一種或多種式VII所示化合物選自式VII1-VII6所示化合物組成的群組，
其中，R101各自獨立地表示碳原子數為2-6烷基。 Wherein, R 101 each independently represent an alkyl group with 2-6 carbon atoms.
D.液晶顯示元件或液晶顯示器包含前述液晶組合物，所述液晶顯示元件或液晶顯示器為主動矩陣顯示元件或顯示器或者被動矩陣顯示元件或顯示器。 D. A liquid crystal display element or a liquid crystal display comprising the aforementioned liquid crystal composition, and the liquid crystal display element or liquid crystal display is an active matrix display element or display or a passive matrix display element or display.
可選的，所述液晶顯示元件或液晶顯示器較佳為主動矩陣尋址液晶顯示元件或液晶顯示器。 Optionally, the liquid crystal display element or liquid crystal display is preferably an active matrix addressing liquid crystal display element or liquid crystal display.
可選的，所述主動矩陣顯示元件或顯示器具體為TN-TFT或IPS-TFT液晶顯示元件或顯示器。 Optionally, the active matrix display element or display is specifically a TN-TFT or IPS-TFT liquid crystal display element or display.
本申請的液晶顯示元件或液晶顯示器藉由含有前述的液晶組合物從而具有高透過率、反應速度快的特點，能夠有效的降低背光能耗。 The liquid crystal display element or liquid crystal display of the present application has the characteristics of high transmittance and fast response speed by containing the aforementioned liquid crystal composition, and can effectively reduce backlight energy consumption.
為了更清楚地說明本發明，下面結合較佳實施例對本發明做進一步的說明。本領域中具有通常知識者應當理解，下面所具體描述的內容是說明性的而非限制性的，不應以此限制本發明的保護範圍。 In order to illustrate the present invention more clearly, the present invention will be further described below in conjunction with preferred embodiments. Those skilled in the art should understand that the specific description below is illustrative rather than restrictive, and should not limit the protection scope of the present invention.
本發明中，製備方法如無特殊說明則均為常規方法，所用的原料如無特別說明均可從揭露的商業途徑獲得，百分比均是指質量百分比，溫度為 攝氏度(℃)，液晶化合物也成為液晶單體，其他符號的具體意義及測試條件如下：Cp表示液晶清亮點(℃)，DSC定量法測試；△n表示光學各向異性，△n=ne-no，其中，no為尋常光的折射率，ne為非尋常光的折射率，測試條件為25±2℃，589nm，阿貝折射儀測試；△ε表示介電各向異性，△ε=ε∥-ε⊥，其中，ε∥為平行於分子軸的介電常數，ε⊥為垂直於分子軸的介電常數，測試條件為25±0.5℃，20微米平行盒，INSTEC：ALCT-IR1測試；γ1表示旋轉黏度(mPa．s)，測試條件為25±0.5℃，20微米平行盒，INSTEC：ALCT-IR1測試；製備液晶組合物所用的設備和儀器為：(1)電子精密天平(精確度0.1mg)(2)不銹鋼燒杯：用於稱量液晶單體(3)勺子：用於加入液晶單體(4)磁力轉子：用於攪拌(5)控溫電磁攪拌器。 In the present invention, the preparation method is a conventional method unless otherwise specified, and the raw materials used can be obtained from disclosed commercial channels unless otherwise specified. Liquid crystal monomer, the specific meanings and test conditions of other symbols are as follows: Cp means liquid crystal clearing point (°C), tested by DSC quantitative method; △n means optical anisotropy, △n=n e -n o , where n o is The refractive index of ordinary light, ne is the refractive index of extraordinary light, the test condition is 25±2℃, 589nm, Abbe refractometer test; △ε means dielectric anisotropy, △ε=ε∥-ε⊥, Among them, ε∥ is the dielectric constant parallel to the molecular axis, ε⊥ is the dielectric constant perpendicular to the molecular axis, the test condition is 25±0.5°C, 20 micron parallel box, INSTEC: ALCT-IR1 test; γ1 means rotational viscosity (mPa.s), the test condition is 25±0.5°C, 20 micron parallel box, INSTEC: ALCT-IR1 test; the equipment and instruments used to prepare the liquid crystal composition are: (1) electronic precision balance (accuracy 0.1mg) ( 2) Stainless steel beaker: for weighing liquid crystal monomers (3) spoon: for adding liquid crystal monomers (4) magnetic rotor: for stirring (5) temperature-controlled electromagnetic stirrer.
液晶組合物的製備方法包括以下步驟：(1)將所用液晶單體按順序擺放整齊；(2)把不銹鋼燒杯放置在天平上，用小勺將單體盛入不銹鋼燒杯中；(3)依次按所需重量添加液晶單體；(4)把加好液晶單體的不銹鋼燒杯放置在電磁攪拌器上加熱融化； (5)待不銹鋼燒杯中混合物大部份融化後，往不銹鋼燒杯中加入一顆磁力轉子，將混合物攪拌均勻，冷卻到室溫後即得液晶組合物。 The preparation method of the liquid crystal composition comprises the following steps: (1) arranging the liquid crystal monomers in order; (2) placing the stainless steel beaker on the balance, and filling the monomer into the stainless steel beaker with a spoon; (3) Add the liquid crystal monomer in turn according to the required weight; (4) place the stainless steel beaker with the liquid crystal monomer on the electromagnetic stirrer to heat and melt; (5) After most of the mixture in the stainless steel beaker is melted, a magnetic rotor is added to the stainless steel beaker, the mixture is stirred evenly, and the liquid crystal composition is obtained after cooling to room temperature.
本發明實施例液晶單體結構用代碼表示，液晶環結構、端基、連接基團的代碼表示方法見下表1、表2。 The structure of the liquid crystal monomer in the embodiment of the present invention is represented by a code, and the code representation methods of the liquid crystal ring structure, terminal group, and linking group are shown in Table 1 and Table 2 below.
舉例： Example:
式I所示的化合物的合成路線 The synthetic route of the compound shown in formula I
前述式I所示的化合物可選擇但不限於採用如下合成路徑來進行合成：
上述合成路線中，R表示環丙基、環戊基或者碳原子數為2-10的烷基中的一個以上的-CH2-被亞環丙基或亞環戊基取代後得到的基團；Y表示OCF3、CF3、CF2H或OCF2H；
上述路線中，原料
上述所有方法的所有步驟的反應均在溶劑中進行；所述溶劑均選自四氫呋喃、N,N-二甲基甲醯胺、二甲亞碸、乙醇、甲醇、二氯甲烷、丙酮、甲苯和去離子水中的至少一種。 The reactions of all the steps of the above-mentioned methods are carried out in a solvent; the solvent is selected from tetrahydrofuran, N,N-dimethylformamide, dimethylsulfoxide, ethanol, methanol, dichloromethane, acetone, toluene and at least one of deionized water.
實施例1、式I1a所示化合物 Compound shown in embodiment 1, formula I1a
步驟1 step 1
2L三口瓶中加入39g(0.30mol)2,3-二氟苯酚、33g(0.33mol)環戊基甲醇、91.7g(0.35mol)三苯基膦及500ml四氫呋喃，攪拌至全溶，氮氣保護下降溫至0-10℃時，滴加61g(0.35mol)偶氮二甲酸二乙酯的300ml四氫呋喃溶液，保溫0-10℃，半小時加完，室溫攪拌4小時；反應液加入500ml水和300ml甲苯攪拌10min，靜置分液，水層用300ml×2甲苯萃取，合併有機層，用40%乙醇300ml×2洗滌後，再用300ml×2飽和食鹽水洗滌，減壓旋乾溶劑，所得液體加200ml石油醚過管柱，再用400ml石油醚沖管柱，旋乾溶劑，減壓蒸餾，得淺黃色液體產品(1-a)50g，GC：97.0%，收率78%。 Add 39g (0.30mol) of 2,3-difluorophenol, 33g (0.33mol) of cyclopentylmethanol, 91.7g (0.35mol) of triphenylphosphine and 500ml of tetrahydrofuran into a 2L three-neck flask, stir until completely dissolved, and place under nitrogen protection When the temperature is lowered to 0-10°C, add 61g (0.35mol) diethyl azodicarboxylate in 300ml tetrahydrofuran dropwise, keep warm at 0-10°C, add half an hour, stir at room temperature for 4 hours; add 500ml water and Stir 300ml of toluene for 10min, let stand to separate the liquid, extract the aqueous layer with 300ml×2 toluene, combine the organic layer, wash with 300ml×2 of 40% ethanol, wash with 300ml×2 saturated saline, and spin dry the solvent under reduced pressure to obtain Add 200ml of petroleum ether to the liquid to pass through the column, then flush the column with 400ml of petroleum ether, spin to dry the solvent, and distill under reduced pressure to obtain 50g of light yellow liquid product (1-a), GC: 97.0%, yield 78%.
步驟2 step 2
1L三口瓶中加入50g(0.24mol)(1-a)及300mL四氫呋喃，開始攪拌，充氮氣置換空氣，置於低溫槽中用液氮降溫，降至-78℃時，滴加2.5M丁基鋰104ml(0.26mol)，20分鐘滴畢，保溫反應半小時後，仍在-78℃滴加28g(0.26mol)硼酸三甲酯的100ml四氫呋喃溶液，20分鐘加完，得到透明溶液，撤去低溫槽，自然升溫至-20℃時(用時2小時)倒入有100ml鹽酸的750ml去離子水中水解，分液，水相用500ml乙酸乙酯萃取一次，合併有機層，水洗至中性。減壓下蒸淨溶劑，加入150ml石油醚，加熱煮沸，冷卻後過濾得到白色固體(1-b)40g，收率：66%。 Add 50g (0.24mol) (1-a) and 300mL tetrahydrofuran into a 1L three-necked flask, start stirring, fill with nitrogen to replace the air, place it in a low-temperature tank and cool it with liquid nitrogen, and when it drops to -78°C, add 2.5M butyl Lithium 104ml (0.26mol), 20 minutes to drop, after half an hour of heat preservation reaction, still dropwise add 28g (0.26mol) trimethyl borate solution in 100ml tetrahydrofuran at -78°C, add 20 minutes to get a transparent solution, remove the low temperature tank, when the temperature was naturally raised to -20°C (2 hours), it was poured into 750ml deionized water with 100ml hydrochloric acid for hydrolysis, liquid separation, the aqueous phase was extracted once with 500ml ethyl acetate, the organic layers were combined, and washed until neutral. The solvent was evaporated under reduced pressure, 150ml of petroleum ether was added, heated to boil, cooled and filtered to obtain 40g of white solid (1-b), yield: 66%.
步驟3 step 3
1L三口瓶中加入48.6g(0.20mol)2-氟-4-溴三氟甲基苯及250mL四氫呋喃，開始攪拌，充氮氣置換空氣，置於低溫槽中用液氮降溫，降至-78℃時，滴加2.5M二異丙胺基鋰石油醚溶液88ml(0.22mol)，半小時加完，反應半小時後，仍在-78℃滴加27g(0.25mol)硼酸三甲酯的50ml四氫呋喃溶液，半小時加完，得到透明溶液，撤去低溫槽，自然升溫至-20℃時(用時2小時)倒入有100ml鹽酸的750ml去離子水中水解，分液，水相用500ml乙酸乙酯萃取一次，合併有機層，水洗至中性。減壓下蒸淨溶劑，加入150ml石油醚，加熱煮沸，冷卻後過濾得到白色固體(1-c)40g，HPLC：96.8%，收率：70%。 Add 48.6g (0.20mol) 2-fluoro-4-bromotrifluoromethylbenzene and 250mL tetrahydrofuran into a 1L three-necked flask, start stirring, fill with nitrogen to replace the air, place in a cryogenic tank and cool down with liquid nitrogen to -78°C 88ml (0.22mol) of 2.5M lithium diisopropylamine petroleum ether solution was added dropwise, and the addition was completed in half an hour. After half an hour of reaction, 27g (0.25mol) of trimethyl borate in 50ml of tetrahydrofuran was added dropwise at -78°C After half an hour, a transparent solution was obtained, and the low-temperature tank was removed, and when the temperature was naturally raised to -20°C (2 hours), it was poured into 750ml of deionized water with 100ml of hydrochloric acid for hydrolysis, separated, and the aqueous phase was extracted with 500ml of ethyl acetate Once, the organic layers were combined and washed with water until neutral. The solvent was evaporated under reduced pressure, 150ml of petroleum ether was added, heated to boil, cooled and filtered to obtain 40g of white solid (1-c), HPLC: 96.8%, yield: 70%.
步驟4 step 4
1L三口瓶中加入40g(0.14mol)(1-c)及300mL四氫呋喃攪拌至全溶，加入60g雙氧水攪拌均勻加熱回流5h；停止反應，冷卻至室溫，加入300ml二氯甲烷，振盪分液，水層用300ml×2二氯甲烷萃取，合併二氯甲烷，用300ml×2飽和氯化鈉水溶液洗滌後經25g無水硫酸鈉乾燥後旋乾溶液，得淺黃色液體(1-d)29g，GC：95.2%，收率81%。 Add 40g (0.14mol) (1-c) and 300mL tetrahydrofuran into a 1L three-necked flask and stir until completely dissolved, then add 60g hydrogen peroxide and stir evenly, heat to reflux for 5 hours; stop the reaction, cool to room temperature, add 300ml dichloromethane, shake and separate the liquid, The aqueous layer was extracted with 300ml×2 dichloromethane, combined with dichloromethane, washed with 300ml×2 saturated aqueous sodium chloride solution, dried with 25g of anhydrous sodium sulfate, and then spin-dried to obtain 29g of light yellow liquid (1-d), GC : 95.2%, yield 81%.
步驟5 step 5
1L三口瓶中加入25.6g(0.10mol)(1-b)、25.9g(0.10mol)(1-d)、26.5g(0.25mol)碳酸鈉、300ml甲苯、300ml乙醇和150ml純水攪拌至全溶，氮氣保護下加入0.15g四(三苯基膦)鈀，加熱回流反應5h；停止反應，加300ml純水攪拌分液，水層用200ml×2甲苯萃取，合併有機層，用300ml×2飽和食鹽水洗滌，減壓旋乾溶劑，所得液體加150g石油醚攪拌均勻，-20℃冷凍1小時，得白色固體(1-e)30g，GC：99.0%，收率77%。 Add 25.6g (0.10mol) (1-b), 25.9g (0.10mol) (1-d), 26.5g (0.25mol) sodium carbonate, 300ml toluene, 300ml ethanol and 150ml pure water into a 1L three-necked flask and stir until completely Add 0.15g of tetrakis(triphenylphosphine) palladium under the protection of nitrogen, heat and reflux for 5h; stop the reaction, add 300ml of pure water to stir and separate the liquids, extract the aqueous layer with 200ml×2 toluene, combine the organic layers, and use 300ml×2 Wash with saturated brine, spin dry the solvent under reduced pressure, add 150 g of petroleum ether to the obtained liquid, stir well, and freeze at -20°C for 1 hour to obtain 30 g of white solid (1-e), GC: 99.0%, yield 77%.
步驟6 step 6
在500ml三口瓶中加入30g(0.077mol)(1-e)，氮氣保護下加入200ml二甲基亞碸(DMSO)，攪拌均勻，加入6.0g(0.15mol)60%氫化鈉礦物油， 加熱至120℃攪拌4小時；停止反應，冷卻至室溫，將反應液倒入300g冰水中攪拌，析出固體，濾布吸濾得固體，晾乾，加200ml石油醚加熱全溶後過30g熱矽膠管柱，用200ml熱石油醚沖管柱，旋乾溶液，1倍甲苯和2倍石油醚加熱全溶，0℃再結晶兩次，得白色固體(I1a)13g，GC：99.85%，收率45%。 Add 30g (0.077mol) (1-e) into a 500ml three-necked flask, add 200ml dimethylsulfoxide (DMSO) under nitrogen protection, stir evenly, add 6.0g (0.15mol) 60% sodium hydride mineral oil, Heat to 120°C and stir for 4 hours; stop the reaction, cool to room temperature, pour the reaction solution into 300g of ice water and stir, the solid precipitates, filter the solid with filter cloth, dry it in the air, add 200ml of petroleum ether to dissolve completely, and pass through 30g of hot water Flush the silica gel column with 200ml of hot petroleum ether, spin the solution, heat 1 times toluene and 2 times petroleum ether to completely dissolve, and recrystallize twice at 0°C to obtain 13g of a white solid (I1a), GC: 99.85%. The rate is 45%.
式I1a所示化合物的光學各向異性體△n為0.135，介電各向異性為△ε為-3.1，垂直介電常數ε⊥為23.2。 The optical anisotropy Δn of the compound represented by formula I1a is 0.135, the dielectric anisotropy is Δε is -3.1, and the vertical permittivity ε ⊥ is 23.2.
實施例2、式I1b所示化合物 Compound shown in embodiment 2, formula I1b
步驟1 step 1
以3-丙基環戊基甲醇替代環戊基甲醇為原料，參考實施例1中步驟1合成 Using 3-propylcyclopentylmethanol instead of cyclopentylmethanol as raw material, refer to step 1 synthesis in Example 1
步驟2 step 2
以(2-a)為原料，參考實施例1中步驟2合成
步驟3 step 3
以(2-b)和(1-d)為原料，參考實施例1中步驟5合成
步驟4 step 4
以(2-c)為原料，參考實施例1中步驟6合成I1b
式I1b所示化合物的光學各向異性體△n為0.134，介電各向異性為△ε為-3.1，垂直介電常數ε⊥為23.3。 The optical anisotropy Δn of the compound shown in formula I1b is 0.134, the dielectric anisotropy is Δε is -3.1, and the vertical permittivity ε ⊥ is 23.3.
實施例3、式I4a所示化合物 Compound shown in embodiment 3, formula I4a
步驟1 step 1
以2-氟-4-溴三氟甲氧基苯替代2-氟-4-溴三氟甲基苯為原料，參考實施例1中步驟3合成
步驟2 step 2
以(3-a)為原料，參考實施例1中步驟4合成
步驟3 step 3
以(1-b)和(3-b)為原料，參考實施例1中步驟5合成
式I4a所示化合物的光學各向異性體△n為0.113，介電各向異性為△ε為-3.2，垂直介電常數ε⊥為18.2。 The optical anisotropy Δn of the compound represented by formula I4a is 0.113, the dielectric anisotropy is Δε is -3.2, and the vertical permittivity ε ⊥ is 18.2.
實施例4、式I4c所示化合物 Compound shown in embodiment 4, formula I4c
步驟1 step 1
以環丙基甲醇替代環戊基甲醇為原料，參考實施例1中步驟1合成
步驟2 step 2
以(4-a)為原料，參考實施例1中步驟2合成
步驟4 step 4
以(4-c)為原料，參考實施例1中步驟6合成I4c
式I4c所示化合物的光學各向異性體△n為0.115，介電各向異性為△ε為-3.3，垂直介電常數ε⊥為19.2。 The optical anisotropy Δn of the compound represented by formula I4c is 0.115, the dielectric anisotropy is Δε is -3.3, and the vertical permittivity ε ⊥ is 19.2.
實施例5、液晶組合物 Embodiment 5, liquid crystal composition
液晶組合物的配方及相應的性能如下表3所示。 The formula and corresponding properties of the liquid crystal composition are shown in Table 3 below.
對比例1 Comparative example 1
液晶組合物的配方及相應的性能如下表4所示。 The formula and corresponding properties of the liquid crystal composition are shown in Table 4 below.
由實施例5與對比例1對比，相對於不含式II所示的化合物的對比例1，含有式II所示化合物的實施例5的液晶組合物的垂直介電常數ε⊥得到了明顯的提高，從而能夠提高液晶組合物透過率。 By comparing Example 5 with Comparative Example 1, relative to Comparative Example 1 that does not contain the compound shown in Formula II, the vertical dielectric constant ε ⊥ of the liquid crystal composition of Example 5 containing the compound shown in Formula II has been significantly improved. Improve, so that the transmittance of the liquid crystal composition can be improved.
對比例2 Comparative example 2
液晶組合物的配方及相應的性能如下表5所示。 The formula and corresponding properties of the liquid crystal composition are shown in Table 5 below.
由實施例6與對比例2的比較可知，相對於液晶組合物中使用末端基團為直鏈烷氧基的二苯並呋喃結構化合物的對比例2，含有末端基團為環戊基、環丙基取代烷基的二苯並呋喃結構化合物的實施例6的液晶組合物具有更高的清亮點和更高的溶解性。 From the comparison of Example 6 and Comparative Example 2, it can be seen that, compared with Comparative Example 2, which uses a dibenzofuran structure compound whose terminal group is a linear alkoxy group in the liquid crystal composition, the terminal group contains cyclopentyl, ring The liquid crystal composition of Example 6 of the dibenzofuran structure compound substituted with propyl group has higher clearing point and higher solubility.
實施例6 Example 6
液晶組合物的配方及相應的性能如下表6所示。 The formula and corresponding properties of the liquid crystal composition are shown in Table 6 below.
實施例7 Example 7
液晶組合物的配方及相應的性能如下表7所示。 The formula and corresponding properties of the liquid crystal composition are shown in Table 7 below.
實施例8 Example 8
液晶組合物的配方及相應的性能如下表8所示。 The formula and corresponding properties of the liquid crystal composition are shown in Table 8 below.
實施例9 Example 9
液晶組合物的配方及相應的性能如下表9所示。 The formula and corresponding properties of the liquid crystal composition are shown in Table 9 below.
實施例10 Example 10
液晶組合物的配方及相應的性能如下表10所示。 The formula and corresponding properties of the liquid crystal composition are shown in Table 10 below.
實施例11 Example 11
液晶組合物的配方及相應的性能如下表11所示。 The formula and corresponding properties of the liquid crystal composition are shown in Table 11 below.
實施例12 Example 12
液晶組合物的配方及相應的性能如下表12所示。 The formula and corresponding properties of the liquid crystal composition are shown in Table 12 below.
實施例13 Example 13
液晶組合物的配方及相應的性能如下表13所示。 The formula and corresponding properties of the liquid crystal composition are shown in Table 13 below.
實施例14 Example 14
液晶組合物的配方及相應的性能如下表14所示。 The formula and corresponding properties of the liquid crystal composition are shown in Table 14 below.
實施例15 Example 15
液晶組合物的配方及相應的性能如下表15所示。 The formula and corresponding properties of the liquid crystal composition are shown in Table 15 below.
實施例16 Example 16
液晶組合物的配方及相應的性能如下表16所示。 The formula and corresponding properties of the liquid crystal composition are shown in Table 16 below.
實施例17 Example 17
液晶組合物的配方及相應的性能如下表17所示。 The formula and corresponding properties of the liquid crystal composition are shown in Table 17 below.
實施例18 Example 18
液晶組合物的配方及相應的性能如下表18所示。 The formula and corresponding properties of the liquid crystal composition are shown in Table 18 below.
實施例19 Example 19
液晶組合物的配方及相應的性能如下表19所示。 The formula and corresponding properties of the liquid crystal composition are shown in Table 19 below.
實施例20 Example 20
液晶組合物的配方及相應的性能如下表20所示。 The formula and corresponding properties of the liquid crystal composition are shown in Table 20 below.
實施例21 Example 21
液晶組合物的配方及相應的性能如下表21所示。 The formula and corresponding properties of the liquid crystal composition are shown in Table 21 below.
實施例22 Example 22
液晶組合物的配方及相應的性能如下表22所示。 The formula and corresponding properties of the liquid crystal composition are shown in Table 22 below.
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